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mr.crow
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Local Anesthetics
Having recently been to the dentist I am now interested in local anesthetics. Particularly benzocaine and procaine (well, a variation called
dimethylprocaine). Novocaine is basically a wonderdrug. The nitrous oxide didn't do shit.
I have two questions regarding the synthesis:
Acyl chloride alcoholysis
4-nitrobenzoyl chloride is reacted with ethanol or 2-dimethylamino ethanol. Obviously under anhydrous conditions.
What do I use for a solvent? The acyl chloride is a solid.
What do I use for a proton scavenger to get rid of the HCl formed? I do not have pyridine or triethylamine. yuck. Can excess 2-dimethylamino ethanol
be used?
Reduction of aromatic nitro
Reacted with water, Fe filings and HCl. Similar to the synthesis of aniline from nitrobenzene. Would this degrade the ester bond at all? How do I
isolate the product from the iron junk, with solvent extraction?
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The WiZard is In
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Quote: Originally posted by mr.crow  | Having recently been to the dentist I am now interested in local anesthetics. Particularly benzocaine and procaine (well, a variation called
dimethylprocaine). Novocaine is basically a wonderdrug. The nitrous oxide didn't do shit.
I have two questions regarding the synthesis: |
If you have an catalytic reduction apparatus at hand -
you can shake ethy p-nitrobenzoate in 95% alcohol with
hydrogen and a platinum oxide catalysis.
Details can be had in :—
Organic Synthesis
Collective Volume 1
p. 240
---
Why do I get the feeling you have not researched this?
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hissingnoise
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| Quote: | | Why do I get the feeling you have not researched this? |
Numbness . . . ?
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mr.crow
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That's why its the beginning section. I can't do hydrogenation under pressure. Atmospheric may be OK
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Sedit
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Ozone labs performed a synthesis of Benzocaine IIRC. Look thru our search engine to find it.
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
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smuv
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you can reduce that nitro group no problem with either PtO2, Pt/C or Pd/C at atmospheric pressure. Pd/C and Pt/C are acidic enough to catalyze
(trans)esterefications, so choose your solvents carefully.
Edit: also nitrobenzoic acids are very easy to esterify...so...it is a very doable synth. Additionally, if you want to avoid the nitro-compound, you
can just buy para-amino benzoic acid as a health suppliment. But if you want to take that route, you can just buy benzocaine OTC (sensitive condoms,
tooth ache drops, throat anaesthetic for blowjobs).
[Edited on 5-16-2011 by smuv]
"Titanium tetrachloride…You sly temptress." --Walter Bishop
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The WiZard is In
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Hey - No Pain No Gain. I am sure after you make one of these
you will find lots of uses for it..... if not — a present for that
special someone - sell it on eBay - donate it to charity and
take a US $73 867.49 tax deduction.
      
If science was easy anyone could do it and we would all
be out of jobs. Well - perhaps not me. I am retired so
now I sit home and they send me money. However, I
am always careful to open my pension check with rubber
gloves on — the company puts a slow acting poison on them
so their retirees will not collect for long. I am given to
understand that they are working on a digital poison for those
who get their pensions via EFT.
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Morgan
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I read a science article of a woman who was put under with nitrous oxide and developed permanent tinnitus after the operation. Certain antibiotics can
be ototoxic too.
http://en.wikipedia.org/wiki/Ototoxicity
Drugs that can cause tinnitus
Anesthetics
• bupivacain
• tetracain
• lidocaine (Novacaine)
http://www.hearingaiddocs.com/sites/default/files/OtotoxicBr...
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The WiZard is In
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Bing and the little light in the back of whats left of my
mind goes off.
Removed en bloc from PubMed
Leg J. 1990;58 ( Pt 1):29-34.
Fantasies during sedation with intravenous midazolam or diazepam.
Dundee JW.
Source
Queen's University of Belfast.
Abstract
Details are reported of 41 incidents where women reported fantasies during sedation with IV midazolam or diazepam: 27 of them had some sexual element
and 20 were unpleasant experiences. The events occurred in a logical sequence and all were certain of their authenticity. Some led to litigation
against the sedationist. Out of 25 verified reports made by patients of incidents occurring during sedation, 17 did not happen and in 9/13 clear
descriptions there was some relation between the fantasy and something that really happened under sedation. All occurred with what are now considered
large doses of the drugs. During or following sedation lady patients should not be treated or examined without the presence of a responsible third
person. The use of the injectable benzodiazepines, diazepam and more recently midazolam, with their sedative, amnesic and relaxing properties have
made unpleasant operative procedures, particularly those usually carried out under local analgesia, more acceptable to many patients. These include
oral endoscopy and dental procedures and operations under spinal or epidural analgesia. These drugs also provide good sedation during ventilatory
support and in the intensive care unit. Over a long period of time these benzodiazepines have proven to be, in appropriate doses, among the safest in
medicine for short term use. There have however been a few cases of what can be described as "fantasies" occurring during sedation: events occurring
in a logical sequence which are very real to the patient and yet, on the evidence of two or more independent witnesses, did not occur. Many of these
have had an element of sexual trespass.(ABSTRACT TRUNCATED AT 250 WORDS)
There dobe others.
---------
Extracted from —
TEACHING VAGINAL EXAMINATION
The Lancet
1988, ii. (8624):1375
The use for anaesthetised and possibly uninformed patients for reaching medical students pelvic examination skills cannot be justified. Consent should
certainly be sought. The argument that anaesthetised patients are easier to examine [9] suggests that students may learn more about the examination
when patents are asleep a concept rejected by many gynaecologists and certainly not supported by published findings. The American experience: of
using volunteers, who can talk to the students and thus assist with the teaching session, is far more practical and possibly more beneficial.
Certainly, examining an awake patient is more realistic.
Since many UK medical students appear still to be gaining their first experience: of vaginal examination upon unconscious patients, and since the
views of patients are now known, a systematic examination of this issue would appear to be desirable.
[They could go home and practice on their drunk/stoned GF's.]
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mr.crow
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Ok back on topic! How is this for a basic procedure?
1) Dissolve 4-nitrobenzoyl chloride in toluene
2) Drip toluene solution into excess ethanol (stirring, anhydrous, etc). Reflux. HCl will be liberated
3) Isolate product? Remove toluene and ethanol?
4) Add catalyst and hydrogenate at STP. Ethanol for solvent
Obviously im not going to do anything without looking at a real reference, but I would still like you guys' input
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Sedit
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Not 100% sure but hydrogenation seems excessive in this case when I would assume a dissolving metal readuction to proceed fine.
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
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Ozone
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IIRC, we made lidocaine (2nd year Organic lab) from reacting 2,4-dimethylaniline with chloroacetyl chloride. The product was isolated by filtration
dried and dissolved in toluene. This was reacted with diethylamine and then refluxed. I have attached a procedure.
This synthesis was straight forward and the yields were good. The question is more a matter of sourcing/preparing the chemicals (which are all
difficult/controlled).
Cheers,
O3
[edit] attaching file 
[Edited on 17-5-2011 by Ozone]
Attachment: Lidocaine synthesis.doc (46kB)
This file has been downloaded 5194 times
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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mr.crow
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ethyl acetate can also be used as a solvent for 4-nitrobenzoyl chloride
Yeah hydrogenation sounds like a pain. The acid might trash the ester bond. Maybe a ethanol/water solvent mixture would work
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The WiZard is In
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| Quote: Originally posted by mr.crow | Having recently been to the dentist I am now interested in local anesthetics. Particularly benzocaine and procaine (well, a variation called
dimethylprocaine). Novocaine is basically a wonderdrug. The nitrous oxide didn't do shit.
I have two questions regarding the synthesis: |
When I purchased my copy to the 14th edition of The Merck
Index it came with a CD allowing internet access for one year,
I never got around to/had reason to install it — until now.
Monograph Number: 0001086
Title: Benzocaine
CAS Registry Number: 94-09-7
CAS Name: 4-Aminobenzoic acid ethyl ester
Additional Names: ethyl aminobenzoate
Trademarks: Americaine (Medeva); Anaesthesin (Ritsert); Flavamed (Berlin-Chemie); Subcutin (Ritsert)
Molecular Formula: C9H11NO2
Molecular Weight: 165.19
Percent Composition: C 65.44%, H 6.71%, N 8.48%, O 19.37%
Literature References: Prepd by the esterification of p-aminobenzoic acid: Salkowski, Ber. 28, 1921 (1895); Vorländer, Meyer, Ann. 320, 135 (1902);
by the reduction of ethyl p-nitrobenzoate: Limpricht, ibid. 303, 278 (1898); R. Adams, F. L. Cohen, Org. Synth. coll. vol. I, 240 (2nd ed., 1941).
In industrial practice the reducing agent is usually iron and water in the presence of a little acid. Comprehensive description: S. L. Ali, Anal.
Profiles Drug Subs. 12, 73-104 (1983).
Properties: Rhombohedra from ether, mp 88-90°. Stable in air. One gram dissolves in about 2500 ml water, 5 ml alcohol, 2 ml chloroform, in about 4
ml ether, and in 30 to 50 ml of expressed almond oil or olive oil. Also sol in dil acids. pKa 2.5.
Melting point: mp 88-90°
pKa: pKa 2.5
Therap-Cat: Anesthetic (local).
Therap-Cat-Vet: Local (usually surface) anesthetic.
Keywords: Anesthetic (Local).
Monograph Number: 0007757
Title: Procaine
CAS Registry Number: 59-46-1
CAS Name: 4-Aminobenzoic acid 2-(diethylamino)ethyl ester
Additional Names: p-aminobenzoyldiethylaminoethanol; 2-diethylaminoethyl p-aminobenzoate
Molecular Formula: C13H20N2O2
Molecular Weight: 236.31
Percent Composition: C 66.07%, H 8.53%, N 11.85%, O 13.54%
Literature References: Benzoic acid derivative with anesthetic activity. Prepn: A. Einhorn, US 812554 (1906); idem, Ann. 371, 125 (1909); A.
Einhorn, E. Uhlfelder, ibid. 131. CNS effects: C. G. Peterson, Anesthesiology 16, 976 (1955). Intravenous pharmacokinetics in humans: A. B. Seifen
et al., Anesth. Analg. 58, 382 (1979). Clinical evaluation as anti-arrhythmic and cough suppressant during anesthesia: D. S. Thompson et al., Am. J.
Surg. 138, 798 (1979). Stabilization of vascular smooth muscle in vitro: K. Kitamura et al., Drugs Exp. Clin. Res. 12, 773 (1986). Toxicity data:
W. C. North, K. F. Urbach, J. Am. Pharm. Assoc. Sci. Ed. 45, 382 (1956); E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).
Properties: Hygroscopic, anhydr plates, tablets from ligroin or ether, mp 61°. When freshly precipitated, one gram dissolves in 200 ml water. Sol
in alc, ether, benzene, chloroform. LD50 in mice (mg/kg): 195 i.p.; 45 i.v. (North, Urbach).
Melting point: mp 61°
Toxicity data: LD50 in mice (mg/kg): 195 i.p.; 45 i.v. (North, Urbach)
Derivative Type: Dihydrate
CAS Registry Number: 6192-89-8
Properties: Needles from aq alc, mp 51°. Slightly bitter taste; applied to the tongue causes transitory numbing sensation.
Melting point: mp 51°
Derivative Type: Nitrate
CAS Registry Number: 6192-92-3
Molecular Formula: C13H20N2O2.HNO3
Molecular Weight: 299.32
Percent Composition: C 52.16%, H 7.07%, N 14.04%, O 26.73%
Properties: Crystals, mp 100-102°. Sol in water, alcohol. The aq soln is neutral. Particularly useful with silver nitrate because no precipitate
forms.
Melting point: mp 100-102°
Derivative Type: Butyrate
CAS Registry Number: 136-55-0
Trademarks: Probutylin (Rorer)
Molecular Formula: C13H20N2O2.C4H8O2
Molecular Weight: 324.42
Percent Composition: C 62.94%, H 8.70%, N 8.63%, O 19.73%
Properties: Hygroscopic crystals. Soluble in water, alcohol, vegetable oils.
Derivative Type: Hydrochloride
CAS Registry Number: 51-05-8
Trademarks: Anestil; Enpro (Kobayashi); Gero (URPAC); Jenacaine; Medaject (Neda); Naucaine; Neocaine; Novocain (Sanofi
Winthrop); Omnicain (Daiichi); Planocaine (M & B); Rocain (Fuso); Syntocain (Sintetica)
Molecular Formula: C13H20N2O2.HCl
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mr.crow
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Thanks WiZard and Ozone
Does Merck have dimethylprocaine? 2-dimethylamino ethanol is one of those health supplements
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mr.crow
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I got my p-nitrobenzoyl chloride in the mail. I put the sealed bottle into a plastic box with NaOH desiccant
Here is a book describing the procedure. Uses toluene as a solvent and adds the alcohol dropwise. Why does it say it can't be stored without
decomposition?
(cant find edit link, double post)
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The WiZard is In
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| Quote: Originally posted by mr.crow | | I got my p-nitrobenzoyl chloride in the mail. I put the sealed bottle into a plastic box with NaOH desiccant. Why does it say it can't be stored
without decomposition? |
La Condensed Chemical Dictionary 14th ed and The Merck Index sez
it dobe decomposed by water and alcohol.... probable sensitive to
moisture in the air. Which is why you put the sealed bottle into a
plastic box with NaOH desiccant.
Monograph Number: 0006590
Title: 4-Nitrobenzoyl Chloride
CAS Registry Number: 122-04-3
Molecular Formula: C7H4ClNO3
Molecular Weight: 185.56
Percent Composition: C 45.31%, H 2.17%, Cl 19.11%, N 7.55%, O 25.87%
Line Formula: NO2C6H4COCl
Literature References: Prepd by the action of phosphorus
pentachloride on p-nitrobenzoic acid: Adams, Jenkins, Org.
Synth. 3, 75 (1923).
Properties: Bright yellow needles from petr ether. Pungent odor.
mp 75°. bp105 205°; bp12 154°. Decomposed by water and
alcohol; sol in ether. Keep well closed.
Melting point: mp 75°
Boiling point: bp105 205°; bp12 154°
Had a spare moment — so I checked the Organic Syntheses ref.
(I used one of the Collective volumes.)
5. The product is best placed while hot in small wide-mouth
bottles and allowed to solidify. This prevents moisture from
the air from decomposing more than the surface layer of the
acid chloride.
djh
----
Diana elected herself the People's
Princess. So she became a godess
for the unfortunate, the silly and the
unhappy.
Phillip Howard
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peach
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Unless you're out for a challenge, start with p-aminobenzoic acid (PABA from health stores) and go to benzocaine. The PABA method is not really hard
or equipment / chemically demanding.
I've run it before and it worked perfectly first time, easy.
It doesn't work as well as injections, sprays or other commercial formulations. Injections immediately defeat a lot of the diffusion / osmosis limits
through most of the tissue and place the drug directly at root nerves, so it disables all the branches from there. When you go to the dentists,
they'll usually inject it at the back of your mouth, because the roots that span out to your jaw pass by there. To block an impulse, approximately
three of the nodes of ranvier need to be jammed up in series on each axon. I think it requires more than one to make sure the propagation doesn't pass
by to the next node, and restart, through the cytoplasm. The nodes function as digital signal buffers, as you'd find on a transatlantic optical fibre
or in numerous bits of electronics. Nerves can only transmit and receive in digital, and at a poor 1kHz peak; versus 300 billion for a state of the
art transistor. They produce a more analogue whole by the summing and subtraction that occurs at the synapses, which are immensely complex and
adaptable.
Injections aren't bad, but my dentist jabbed one of said roots with the blade once, and I certainly felt that. Despite obviously having the blade tip
very close to the nerve when injecting, I could still feel shooting stinging in my arm as he was drilling the tooth, so I had an extra two syringes
worth. 
Even with injections, I find they don't reach the full numbness until tens of minutes later. I'd prefer to sit out in the waiting room for a while.
The preformulated sprays, foams and creams (and injectable solutions) can have additional materials to help them move through skin and tissue better.
As a powder, it's virtually useless on dry or even damp skin. I tried it out on my lip. It did go numb, but definitely not as numb as it would with an
injection and it didn't last very long either. Rather than home brewing my own super aesthetic, I'd actually prefer the preformulated spray bottle
I've got for sore throats.
If you've read around neurons a bit, it's interesting to see how these things actually function on a cellular level and consider what they've made
possible in the word; life changing and saving surgery practically depends on it now. The history of cocaine is quite amusing if you haven't heard how
it came into medical use.
There's a video of the PABA method here. Although I must warn you, the woman's voice is extremely annoying and she's nagging away for
over 8 minutes. <----- clickity click
[Edited on 28-5-2011 by peach]
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mr.crow
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Thanks Peach!
Arghh her voice! could use some lowpass filtering. We need more hot girls in chemistry though.
She makes some bupropion too. hmmm!
Double, double toil and trouble; Fire burn, and caldron bubble
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albqbrian
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A very simple route...
How about just buying it on eBay 
http://cgi.ebay.com/5-grams-Lidocaine-HCl-99-9-Pure-Local-An...
I'm thinking of getting some for my home first aid kit.
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The WiZard is In
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Sting relief swab(s)
I don't have much use for these as I usually get stung
2-3 times a year, most recently 5 minuets ago! Went
do to la shop for a ruler and found a bumblebee on the
floor. Moved it with my boot ... yup still alive ... now on
its back... put my finger down for to climb on... stupid
falls off... extend helping finger again — the SOB stings me!
Last year I got stung 2X - one on my broken nose and then
on my ear by the pictured yellow jackets [nest]. I have built up
an immunity now their stings don't hurt much/long, more
importantly their stings don't itch. The first year I was
here their stings itched for a day or two.
After getting stung 2X I left the door blocked open so they
wouldn't get alarmed when I opened it. We got along fine for
the rest of the season.
Perhaps I can use the swabs for Pizza pallet.
Latter today I will drain half a dozen of so out and evap. the alcohol and weigh. I doubt I'll get 5 grams.
    
[Edited on 29-5-2011 by The WiZard is In]
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The WiZard is In
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Sting relief swabs - a market for - big time
Extracted from —
Biotropica 5(2): 94-101 1973
The Human Use of Insects: Examples from the Yukpal
Kenneth Ruddle
Latin American Center, University of California, Los Angeles, California 90024 U.S.A.
Scanned (An you know what that means!)
[This from when I still went to work for a living and could afford to subscribe.]
INSECTS IN RITUAL.—The vicious wasp Polybia sgnobibs plays a
major symbolic role in the ritual (masuk ape watpo) which follows
the birth of a boy. Shortly after the birth a feast of koses [4] and
sona [5] is prepared. Larvae of P. ignoblis are inserted in a ridge
along the top of the koses. The larvae of this particular wasp are
used because the adult defends itself with an extremely painful
sting when the nest is disturbed. The boy's father's stoicism and
silent resistance in the face of such torture is a sign of his bravery
and masculinity which is thought to be transmitted to the child by
the ritual. The father's agony and, as a consequence thereof, the
child's future desirable qualities are increased by the injunction
that the father depart alone in search of enough wasp's nests to
fulfill his obligation. Furthermore, contrary to everyday
procedures, he is permitted to use neither fire nor smoke to drive
away the incensed adult wasps. During the course of his foraging
he is stung repeatedly. Only when he has returned home is he
permittted to roast the nests and extract the larvae.
---
Roast the nest I guess Revenge is a dish best served
cold [la vengeance se mange très-bien froide] does't work for them.
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The WiZard is In
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Sting Swabs — The numbers are in
The liquid (plus a smidgen of thin glass) obtained from 6 weighs
1.74 grams. So if 80% is inert.... you are going to need ..........!
Somewhere 'bout here I have a dozen or two of the ones
dentists put into their syringes — obtained from some dentists
garbage years ago. (I come from a long line of Irish Horse
Thieves and Garbage Pickers.)
djh
----
What do you call a man
who puts his tools in another
man's mouth?
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peach
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I used to keep honey bees, I still have the hives in the back garden. There were tens of thousands of them per hive, unlike bumble bees who live in
little groups underground. Stings were not all that common provided none of them were squashed, which makes them all angry when they smell another is
being hurt.
The sting, for those who haven't been stung, does not hurt when they actually sting you. It hurts afterwards as the venom begins to spread. It would
vary a lot depending on the clothing. If I had a layer of clothes between them and me, they didn't seen to be able to do much even if they stung me.
But one in particular was really bad. I'd been moving some old hives with some old timer bee keeper in my trainers (without socks or a suit on) and
one of them spotted some bare ankle, and went about stinging it. It got a really good amount in and then I had to stand around chatting to the guy
pretending it was fine, when actually my ankle was throbbing like I'd just twisted it.
If you wipe the sting out of your skin as soon as it does it, they do barely anything. Bees have a lot more character than you'd think only seeing one
or two. When dealing with hives and thousands of them pouring out, some of the colonies are quite clearly a lot more productive or aggressive than
others; which also seems to make them less prone to parasitic infections. They also get much more aggressive if they're not used to human contact, if
the hive has been left for months and months without anyone checking it.
There is a very annoying habit among bee keepers to go on about 'nice' bees, and how they're so 'nice' you don't need to wear a suit; civilised wild
insects. What they mean is 'pussy' bees, which can't defend themselves against infections. And yes... even pussy bees sting. One old guy, after I
questioned him keeping so many in a small back garden, kept going on about how supreme his were because he didn't need a bee suit around them. Minutes
later, he was sulking around rubbing his balding bonce because one, as if having heard what he was saying and not been happy about it, had completely
out the blue flown over and stung his shiny head.
[Edited on 29-5-2011 by peach]
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albqbrian
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A penny for your thoughts...
My backwoods type mother-in-law just was chatting about this. The cure she and her buds swear by is a simple, US copper penny. Immediately put it on
the area that was stung and leave it for 15 min or so.
I guess that it can't hurt (ugh no pun intended) to try. I have to say after living in Asia for several years, I'm a bit more pen minded on medical
solutions. This one seems reasonable. Certainly the copper could somehow react with some component of the venom.
Oh well, you get what you pay for.
[Edited on 30-5-2011 by albqbrian]
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