Sulfur analog of MDMA

[Refluxer]

For some time I have wondered if this analog might be active.

- Se attached structure

I have never read anything about it. I must admit that haven't really gone to the end of the world (more like to the supermarket) to find info on it. If someone has made it, it probably wasn't very active because I can't find it mentioned anywhere.

And yes, I have UTFSE, but I am not very adept at forum searching. So please don't flame me if you have discussed it before.

Has anyone heard about this compound?

 

[nuke]

There is some reasonable assurance from the other 5- and 4-thiolated compounds that the compound will hold some kind of activity, but I don't think we'll know until anyone tastes it.

AFAIK I have never heard of its synthesis or general existence, nor the existence of the obvious precursors. Perhaps it will pop up in the psychedelics index.

 

[EN21]

sci finder research

I just looked in the sci finder : The compound is not known, the normal phenethylamine is also not known. The Thioanalogues of safrol or isosafrol is also unknown, but the aldehyde is mentioned twice:

Preparation of 1,3-benzoxathiole derivatives for treatment of liver disease. Ueyama, Tamio; Matsumoto, Kazuo; Hirase, Joji; Oosugi, Yumi; Ooshima, Hiroichi; Sogawa, Takeshi; Mizuno, Yasuo; Okui, Yoshikazu; Nishino, Minoru; Nishigaito, Toshinori. (Shinnippon Yakuhin Kk, Japan). Jpn. Kokai Tokkyo Koho (1994), 40 pp. CODEN: JKXXAF JP 06293640 A2 19941021 Heisei. Patent written in Japanese. Application: JP 94-18503 19940215. Priority: JP 93-25199 19930215. CAN 123:169595 AN 1995:780252 CAPLUS

Patent Family Information

Patent No. Kind Date Application No. Date
JP 06293640 A2 19941021 JP 1994-18503 19940215

Priority Application
JP 1994-18503 A 19940215
JP 1993-25199 19930215


Abstract

Title compds. I (R = H, F, Cl, cyano, alkyl, alkoxy, amino; n = 1, 2; X = O, S; Y = CS, CH2) and their pharmacol. acceptable salts, useful for treatment of liver disease, were prepd. Thus, stirring 2-mercapto-4-(methylthio)phenol with thiophosgene and aq. NaOH in CHCl3 for 30 min gave 5-methylthio-1,3-benzoxathiole-2-thione (II). II showed 46% inhibition of D-galactosamine-induced hepatic injury at 12.5 mg/kg orally in rats. Formulations contg. I were given.



and

Stabilizing solution for silver halide photographic material and photographic processing using same. Tsuchiya, Ichiro; Haraguchi, Takeshi; Koboshi, Shigeharu. (Konica Co., Japan). Jpn. Kokai Tokkyo Koho (1992), 40 pp. CODEN: JKXXAF JP 04311957 A2 19921104 Heisei. Patent written in Japanese. Application: JP 91-104699 19910410. Priority: . CAN 118:157730 AN 1993:157730 CAPLUS

Patent Family Information

Patent No. Kind Date Application No. Date
JP 04311957 A2 19921104 JP 1991-104699 19910410

Priority Application
JP 1991-104699 19910410


Abstract

The title stabilizing soln. contains one or more benzodioxole derivs., or analogs thereof (Markush structure given). The surface tension of the title material is 15 to 60 dyne/cm at 20°. Compd. I is an example of the said benzodioxole derivs. The title soln. has good storage stability. Also claimed is the title processing method.



So go on guys and try it out!

 

[fastandbulbous]

I don't think that particular compound would do much in terms of entactogenic activity as it seems, from looking through SAR studies etc and drawing my own conclusions, that to get both serotonogis and dopaminergic activity you need an atom in the 3 position that has a lone pair group similar to oxygen. Although sulphur is in the same periodic group as oxygen, it doesn't seem to have the needed electronic confiuration for a similar interaction.

I've attached a jpeg (modified from the O/P's) that I think might be a lot better candidate for an MDMA like drug

 

[Refluxer]

I don't think that particular compound would do much in terms of entactogenic activity as it seems, from looking through SAR studies etc and drawing my own conclusions, that to get both serotonogis and dopaminergic activity you need an atom in the 3 position that has a lone pair group similar to oxygen. Although sulphur is in the same periodic group as oxygen, it doesn't seem to have the needed electronic confiuration for a similar interaction.

I've attached a jpeg (modified from the O/P's) that I think might be a lot better candidate for an MDMA like drug

I don't know much about SAR yet, but I do know that even though sulfur is right below oxygen it is bulkier and has differences when it comes to chemistry.

I saw that in PIHKAL Shulgin has made the compund (#167) 4T-MMDA-2.

Have you ever heard of anyone making the coumpound you attached?

It would be interesting to see studies on this compound, but if it doesn't have advantages over MDMA (either qualitatively, potency or toxicity) I guess it's not really worth the hassle - except legal status, which usually don't last long if it's a good one.

Anyway, thank you very much for your answers!

 

[bigmac74]

Oxygen: 1s2 2s2 2p4
Sulphur: 1s2 2s2 2p6 3s2 3p4
Selenium: 1s2 2s2 2p6 3s2 3p6 3d10 4s2 4p4

^^ does 2p play a role in this? If so, could we use a nitrogen ion with +1 charge? Or am i just being stupid or is it near impossible to synthesize?

Nitrogen: 1s2 2s2 2p3
Nitrogen¹+: 1s2 2s2 2p4

 

[EN21]

Charged (ionic) will most probably not cross the BBB, unless it has an active transport system. (organic cationic transporter OCT or things like the dopamine transporter DAT).