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Bronstein
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Actually it would be pretty interesting to read the original paper on Lefetamine. The reference is J. Pharm. Soc. Japan 80, 283 (1960). That journal
is available online, but it is missing some older issues, and that article is in one of them. Perhaps someone has it in a library nearby?
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Vogelzang
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You missed the one that had a 75% yield and is one of the two that show activity. You didn't find Harald Holck's article either.
Comparison of analgetic activity of 67 arylalkamines with that of morphine and meperidine by the mouse hot plate method
Journal of the American Pharmaceutical Association
Volume 39 Issue 6, Pages 354 - 359
Copyright © 1960 Wiley-Liss, Inc., A Wiley Company
http://www3.interscience.wiley.com/journal/113356336/abstrac...
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Vogelzang
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Just to state more of the obvious, the ja01215a018 article says that some N-alkyl diphenylethylamines have analgesic properties (compare to the
N,N-dimethyl derivative, lefetamine) and Harald Holck was planning on publishing his results on activity of these compounds, which I seem to have
found. Of course, you can use other methods for synthesizing these compounds. I'm just curious about them and don't plan to make them myself. Some
time or other people need narcotic analgesics to control pain from anything from a toothache to cancer. The isonipecaine mentioned in ja01215a018 is
another name for meperidine.
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JohnWW
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Those N-alkyl diphenylethylamines that have worthwhile analgesic (as distinct from stimulant) properties are probably also the ones that also obey
the "morphine rule" for analgesic activity, i.e. having an aromatic ring, attached to a quaternary carbon (i.e. attached to 4 other carbons), one bond
of this itself attached to two (usually) or more carbons in a chain, with the end of this chain attached to a tertiary-amine nitrogen; i.e.
C6H5-C(-C)(-C)-C-C-N(-C)(-C). A diphenylethylamine would have an additional C6H5 attached to the carbon bonded to the other C6H5, as one of its
substituents.
The "morphine rule" includes codeine and morphine extracted from poppy (especially opium poppy) seed-pods, heroin made by acetylating these, and the
synthetic opioids (used because they are much less addictive) such as methadone and mepiridine (demerol). This rule also includes dextromethorphan, a
synthetic opioid used in cough medicines which is also a phenylethylamine derivative like methamphetamine. McMurry's "Organic Chemistry", which I have
uploaded in the Organic Books thread in the References section, has a good depiction of these structures.
[Edited on 30-1-10 by JohnWW]
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manimal
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According to what I have read, phenyl alkyl ketones are difficult to aminate reductively. I wonder if aluminum amalgam would facilitate amination of
desoxybenzoin.
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manimal
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The stable tautonomer would lie with an enamine, no?
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Borohydride
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http://www.sciencedirect.com/science/article/pii/S0040402010...
or petasis reaction
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Borohydride
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BTW the original route was reductive alkylation.
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Sydenhams chorea
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Digging up the references cited in the orgsyn entry for desoxybenzoin showed a peculiar "quick 'n dirty" reduction of benzoin which actually gives rise to a purer product (as claimed by
the author) than what is usually obtained by the common Zn/acid reduction of benzoin.
Also included, not of preparative value, but rather as an illustration, is the isolation of desoxybenzoin from a mixture of ketones obtained by the
dry distillation of calcium phenylacetate and calcium benzoate.
Attachment: Ueber_die_chemische_Natur_des_Desoxybenzoins-Ber_1873.pdf (351kB)
This file has been downloaded 732 times
[Edited on 11-10-2012 by Sydenhams chorea]
Il n'y a point de sots si incommodes que ceux qui ont de l'esprit.
François de La Rochefoucauld.
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SM2
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Kafka,
Depending on where your true interest(s) lie, you can just purchase 1000 4mG. Chlorpheniramine maleate tabs for about 10 bucks ebay. A much better
drug, completely OTC, 100% legal. Look at the similarities in structure. .wikipedia.org/wiki/Chlorphenamine. We already know it has dopamine effect
via NAC shell. http://www.ncbi.nlm.nih.gov/pubmed/9832958.
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Newton2.0
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SM2, that compound bears little resemblance to deoxybenzoin or to lefetamine. And it acts primarily as an H1 agonist, according to Wikipedia and my
own experimentation. I am not seeing any utility in exploring it here.
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clearly_not_atara
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CPM is an H1 antagonist, and while I have thought of a synthesis for lefetamine, I don't think I should post it in a nine-year dead thread
when it's an illegal drug anyway.
I feel kind of conflicted about lefetamine because some studies suggest it gives a weak withdrawal by opioid standards and it has even been trialled
as a replacement therapy like buprenorphine. But it's still a recreational opioid!
https://www.sciencedirect.com/science/article/abs/pii/037687...
https://www.sciencedirect.com/science/article/abs/pii/S00316...
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zed
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Newton2.0..... That post is ten years old. If those guys had a real interest in opiates, they might be cadavers by now.
It is a fairly ominous sign, for a chemist to take a great "personal" interest in opiates. Hard habit to break, when you, are your own connection.
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Newton2.0
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Whoops, that's my bad guys on both counts, namely, beating the dead horse of lefetamine on this forum and yes I meant antagonist but wrote it
incorrectly. I'm new to online forums so I often forget that this is not like having a conversation. The conversations here die and should be left
dead. Roger that.
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karlos³
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Check one of the others threads about lefetamine, metal reduction of benzoin it is called I think, there are two writeups on its synthesis, one by
Sydenhams Chorea and another more recent one by me.
Its a good painkiller, but not as safe as other opioid painkillers are.
Once I took two 400mg doses and got a nasty headache.
But my pa likes to take 150mg capsules against his back pain and it works well for him.
Its euphoric of course, its not a stimulant though, but it has a great abuse potential.
So be careful with it.
I don't recommend abusing it at all though, as it has neurotoxic properties.
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Newton2.0
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I see about 12 immediate analogues for the rest of the benzoin I have.
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karlos³
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Be aware that the enamine/imine formation on desoxybenzoin is one that works very lousy, except under forcing conditions.
Probably one of the worst ketones for forming a schiff's base, besides acetophenone.
You need to either use mol sieves(for low boiling amines) or a dean stark for higher boiling ones like piperidine.
Also, I just got told by a friend that the neurotoxic properties for lefetamine I stated, are probably not really founded very well.
Papers stated by other papers by people citing them to me, who made it appear like facts.
And I repeated that, shame on me!
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zed
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I was always curious about Heinzelmann's Synthesis of N- Methyl-O-Methoxy-Phenyl-Isopropylamine, and it's N-Dimer. O-Methoxy-Methamphetamine was once
an Over-The-Counter decongestant. Now, it seems to have disappeared.
Heinzelmanns classic paper (which eventually led to the listing and restriction of sales of Nitroethane) was followed by a paper which talks about
reacting a second equivalent of the relevant 2-Propanone to form a Di-Phenyl-Isopropyl.... Amine..... Which was purported to be an
analgesic-anesthetic.
Opioid? I'll look for an attachment.
http://www.orgsyn.org/demo.aspx?prep=CV4P0573
Well, I tracked down a patent. Says only that it is a Local Anesthetic. Just curious about the structural relationship, since an amphetamine-like
opioid showed up in a conversation.
https://patents.google.com/patent/US2930731A/en?inventor=Ric...
[Edited on 14-3-2021 by zed]
[Edited on 14-3-2021 by zed]
[Edited on 14-3-2021 by zed]
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zed
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Now, tell me Karlos, about the crappy-ness of forming Shiff bases with acetophenone. I've been wanting to react acetophenone with Nitro-methane. To
form a Nitro-styrene. I found one non-contactable guy, who says it is a slam-dunk. On the other side of the equation, are multitudes....Who say it
isn't possible.
Do you have any insight?
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