Author Topic: Napthylaminopropane, non-neurotoxic SNDRA  (Read 148 times)

Naphyrone

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Napthylaminopropane, non-neurotoxic SNDRA
« on: December 01, 2009, 04:54:58 PM »
Napthylaminopropane, discussion and likely synthesis outline.

First off before I start going into synthesis of this, pharmacology wise I am amazed that this compound isn't the slightest bit neurotoxic like amphetamine and most amphetamine analogs.

Ok, so the initial part will consist of a starting material of 2-naphthaldehyde, then a reaction of nitroethane and methylamine(from hexamine and hcl, byproduct is formic acid)
 in isopropyl alcohol(MgSO4 dry maybe to get over 90% ?) to yeild N2NP.After that reaction, one could do a metal/acid reduction to the N2NP to yeild N2P.
After that a simple formic acid Leuckart reaction should work to give the end product.

Also one could do a one-pot synthesis using Naphthalene-2-carbonitrile as the starting material via MeMgI and NaBH4(http://www.erowid.org/archive/rhodium/chemistry/amphetamine.html)

Now back on the pharmacology information on this compound, it is a non-neurtoxic releasing agent of Serotonin, Dopamine and Norepinephrine.
EC50 values of 3.4 nM, 11.1 nM, and 12.6 nM. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=15677348
I'm sure this compound is relatively safe, I would be weary of a napthylene compound that has a 'beta' ketone(could metabolize to alcohol?) or alcohol(especially)
since it could possibly form a carcinogenic napthylene epoxide like the beta-blocker drug pronethalol.
« Last Edit: December 01, 2009, 05:36:21 PM by Naphyrone »

Enkidu

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Re: Napthylaminopropane, non-neurotoxic SNDRA
« Reply #1 on: December 01, 2009, 10:55:50 PM »
First off before I start going into synthesis of this, pharmacology wise I am amazed that this compound isn't the slightest bit neurotoxic like amphetamine and most amphetamine analogs.

Not necessarily true.

Ok, so the initial part will consist of a starting material of 2-naphthaldehyde

The real problem is synthesizing a 2 subbed naphthalene compound, unless you're just going to buy that precursor.

Vesp

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Re: Napthylaminopropane, non-neurotoxic SNDRA
« Reply #2 on: December 01, 2009, 11:00:38 PM »
Consider the nitration of naphthalene to yeild a 2-nitro product (not sure? might mostly be 1-nitro.. haven't checked) then reducing that to naphthylamine, and turning that into an aldehyde via

http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0139

Seems possible to me at least if the main product for the nitration of naphthalene is 2-nitronaphthalene.
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Enkidu

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Re: Napthylaminopropane, non-neurotoxic SNDRA
« Reply #3 on: December 02, 2009, 12:38:34 AM »
it's 1 subbed

http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch12/ch12-10.html

Edit: and btw, here are Nicoderm's ideas. You can find most of the relevant papers already posted if you know where to look. http://www.sciencemadness.org/talk/viewthread.php?tid=7061&goto=search&pid=81784
« Last Edit: December 02, 2009, 12:57:10 AM by Enkidu »

jon

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Re: Napthylaminopropane, non-neurotoxic SNDRA
« Reply #4 on: January 20, 2010, 03:38:09 AM »
there are a lot of serotonin releasers that whiie realease copius amount of serotinin produce no high mta comes to mind it causes serotonin syndrome it's some powerful but it's not any fun.