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N-(2-(3,4-methylenedioxyphenyl)-1-methylethyl)-1-(3,4-methylenedioxyphenyl)-2-aminopropane.png


BISQUICK
N-(2-(3,4-methylenedioxyphenyl)-1-methylethyl)-1-(3,4-methylenedioxyphenyl)-2-aminopropane
The textbook answer to this is GZ-250B.

Nickell JR, Zheng G, Deaciuc AG, Crooks PA, Dwoskin LP. Phenyl ring-substituted lobelane analogs: inhibition of [³H]dopamine uptake at the vesicular monoamine transporter-2. J Pharmacol Exp Ther. 2011 Mar;336(3):724-33. doi: 10.1124/jpet.110.172882. Epub 2010 Sep 28. PMID: 20876747; PMCID: PMC3061534.
Lee John & Freudenberg Werner, US2355659 (1944 to F Hoffmann La Roche AG).
 
Based on the above, i recommend that you also take a look at the following list of agents:

GZ-793A [1356447-90-9]

Nickell JR, Siripurapu KB, Horton DB, Zheng G, Crooks PA, Dwoskin LP. GZ-793A inhibits the neurochemical effects of methamphetamine via a selective interaction with the vesicular monoamine transporter-2. Eur J Pharmacol. 2017 Jan 15;795:143-149. doi: 10.1016/j.ejphar.2016.12.016. Epub 2016 Dec 13. PMID: 27986625; PMCID: PMC7050634.

Quinlobelane

Vartak, Ashish P.; Gabriela Deaciuc, A.; Dwoskin, Linda P.; Crooks, Peter A. (2010). "Quinlobelane: A water-soluble lobelane analogue and inhibitor of VMAT2". Bioorganic & Medicinal Chemistry Letters. 20 (12): 3584–3587. doi:10.1016/j.bmcl.2010.04.117.

UKCP-110

Beckmann JS, Siripurapu KB, Nickell JR, Horton DB, Denehy ED, Vartak A, Crooks PA, Dwoskin LP, Bardo MT. The novel pyrrolidine nor-lobelane analog UKCP-110 [cis-2,5-di-(2-phenethyl)-pyrrolidine hydrochloride] inhibits VMAT2 function, methamphetamine-evoked dopamine release, and methamphetamine self-administration in rats. J Pharmacol Exp Ther. 2010 Dec;335(3):841-51. doi: 10.1124/jpet.110.172742. Epub 2010 Aug 30. PMID: 20805303; PMCID: PMC2993560.
 
N-(2-(3,4,5-trimethoxyphenyl)-ethyl)-(2-(3,4,5-trimethoxyphenyl)ethyl)amine.png


HARRY_POTTER
N-(2-(3,4,5-trimethoxyphenyl)-ethyl)-(2-(3,4,5-trimethoxyphenyl)ethyl)amine
 
Here's another one of the VMAT-2 inhibitors that looks quite interesting:

4-Benzyl-1-(3,4-dimethoxyphenethyl)piperidine
[15565-25-0]
Nickell JR, Culver JP, Janganati V, Zheng G, Dwoskin LP, Crooks PA. 1,4-Diphenalkylpiperidines: A new scaffold for the design of potent inhibitors of the vesicular monoamine transporter-2. Bioorg Med Chem Lett. 2016 Jul 1;26(13):2997-3000. doi: 10.1016/j.bmcl.2016.05.025. Epub 2016 May 10. PMID: 27212067; PMCID: PMC4946565.
 
I Don't Understand Why I Would Want A VMAT Inhibitor.

Anyway,

(%E2%88%92)-(6aR,10aR)-6,6,9-trimethyl-%203-propyl-6a,7,8,10a-tetrahydro-%206H-benzo[c]chromen-1-ol.png


LESLIE [THC-P]
(6aR,10aR)-6,6,9-trimethyl-%203-propyl-6a,7,8,10a-tetrahydro-%206H-benzo[c]chromen-1-ol

Me gusta.
 
1-(4-propyl-2,5-dimethoxyphenyl)-2-aminoethane.png


CHAD
1-(4-propyl-2,5-dimethoxyphenyl)-2-aminoethane

Not Just A Country In Africa!

I Gave Cousin Schaefer A 1/2 Gram Of This After Sister Carrie's Wedding! (way back when it was still "legal")
 
1-(2,6-dimethoxy-4-(propylthio)phenyl)-2-aminopropane.png


MICHAEL_LEONARD
1-(2,6-dimethoxy-4-(propylthio)phenyl)-2-aminopropane

Come On, Down! You Are The Next Contestant On The Price Is Right.
 
1-phenyl-1-ethylaminocyclohexane.png


CAROLINE_EMILY_PENNINGTON (pce)
1-phenyl-1-ethylaminocyclohexane

I took pce 1x. It kicked my ass.

"A Rose For Emily" (short story)
very, very 😔 sad
 
N-(2-(3,4-methylenedioxy-5-methoxyphenyl)-1-methylethyl)-1-(3,4-methylenedioxy-5-methoxyphenyl)-2-aminopropane.png


NUT_MEGAN
N-(2-(3,4-methylenedioxy-5-methoxyphenyl)-1-methylethyl)-1-(3,4-methylenedioxy-5-methoxyphenyl)-2-aminopropane

pronounced 'newt'
 
1-(4-methoxyphenyl)-1-(4-methoxyphenoxy)-2-methylaminopropane.png


ALL_PMA'DE_UP
1-(4-methoxyphenyl)-1-(4-methoxyphenoxy)-2-methylaminopropane

Only 1/2 Joking.
 
3,4-methylenedioxyphenol.png


SESAMOL
3,4-methylenedioxyphenol

Williamson Ether Named Reaction

3,4-methylenedioxyanisole.png


3,4-methylenedioxyanisole

Etc. Etc Et Cetera
Und so weiter et cetera

1-(2-methoxy-4,5-methylenedioxyphenyl)-2-methylaminopropane.png


SASHA
1-(2-methoxy-4,5-methylenedioxyphenyl)-2-methylaminopropane

Look. That's All I Feel Like Right Now.
 
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2-methylamino-2-(2,3-methylenedioxyphenyl)-cyclohexanone.png


YO!_I_THOUGHT_I_TOLD_YOU_THAT_WE_WON'T_STOP
2-methylamino-2-(2,3-methylenedioxyphenyl)-cyclohexanone
 
Taxil (Tropane-Paxil) (see under RTI-274)
DAT = 3nM, NET = 2nM, SERT = 6nM.

Keverline-Frantz, Kathryn I.; Boja, John W.; Kuhar, Michael J.; Abraham, Philip; Burgess, Jason P.; Lewin, Anita H.; Carroll, F. Ivy (1998). "Synthesis and Ligand Binding of Tropane Ring Analogues of Paroxetine". Journal of Medicinal Chemistry. 41 (2): 247–257. doi:10.1021/jm970669p.

Ogier L, Turpin F, Baldwin RM, Riché F, Law H, Innis RB, Tamagnan G (May 2002). "Rearrangement of a mesylate tropane intermediate in nucleophilic substitution reactions. Synthesis of aza-bicyclo[3.2.1]octane and aza-bicyclo[3.2.2]nonane ethers, imides, and amines". The Journal of Organic Chemistry. 67 (11): 3637–42. doi:10.1021/jo010973x.

Runyon, Scott P.; Burgess, Jason P.; Abraham, Philip; Keverline-Frantz, Kathryn I.; Flippen-Anderson, Judy; Deschamps, Jeffrey; Lewin, Anita H.; Navarro, Hernán A.; Boja, John W.; Kuhar, Michael J.; Carroll, F. Ivy (2005). "Synthesis, structural identification, and ligand binding of tropane ring analogs of paroxetine and an unexpected aza-bicyclo[3.2.2]nonane rearrangement product". Bioorganic & Medicinal Chemistry. 13 (7): 2439–2449. doi:10.1016/j.bmc.2005.01.046.
 
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