🌟🌟 Social 🌟🌟 Rectify's molecular poetry thread

[Rectify]

FANNIE_MAE
1-(2-trifluoromethyl-3,4-methylenedioxyphenyl)-2-aminopropane

 

[Rectify]

FREDDIE_MAC
1-(5-trifluoromethyl-3,4-methylenedioxyphenyl)-2-aminopropane

 

[Smyth2]

I am getting some pramipexole soon. I saw this patent you might be interested in:
"Compounds for reducing excessive intake of food"
Michael Pieper & Joachim Mierau, WO2003028710 (to Boehringer Ingelheim Pharma GmbH and Co KG).

 

[Rectify]

HULU
1-(4-isopropyl-2,6-dimethoxyphenyl)-2-aminopropane

 

[Rectify]

SEMI_SYNTHETIC_ FEMALE_PHEROMONE#4
4-carboisopropoxy-phenol

For Topical And Perfumery Usage. One Of The Finest Scents.

 

[Smyth2]

SEMI_SYNTHETIC_ FEMALE_PHEROMONE#4
4-carboisopropoxy-phenol

For Topical And Perfumery Usage. One Of The Finest Scents.

It reminds me a bit of a phytoestrogen called 4EM, 4-(Ethoxymethyl)phenol [57726-26-8].

Pearce, Virginia; Nawaz, Zafar; Xiao, Wu; Wiedenfeld, David; Boyle, Nick; Smith, Don (2003). "4-Ethoxymethylphenol: a novel phytoestrogen that acts as an agonist for human estrogen receptors". The Journal of Steroid Biochemistry and Molecular Biology. 84 (4): 431–439. doi:10.1016/S0960-0760(03)00064-5.

 

[Rectify]

SSFP#4 Reminds Me Of High Quality Sunscreen!

SAINT_MARK
1-phenyl-1-carboisopropoxy-2-methylaminopropane

 

[Rectify]

OBOVATOLAMINE
1-(2-aminoprop-1-yl)-3,4-methylenedioxy-5-((2-aminopropyl)phenoxy)benzene

From Obovatol, A Constituent Of Magnolia Tree Essential Oil.

"We From The Magnolia." - Juvenile ('of or like Jupiter'), 400 Degreez.

 

[Smyth2]

That looks incredibly hard gimbled.

 

[Rectify]

Maybe.

4-METHYL-FURFURALAMINE
2-(2-methylamino-1-carbomethoxypropyl)-4-methyl-thiophene

Loosely Based On Articane.

 

[Rectify]

Tryptamine + CH3I --> LAH --> DMT

5-MeO-Tryptamine + CH3I --> LAH --> 5-MeO-DMT

Make Me!

 

[Rectify]

BOO
1-(2-methoxy-3,4-methylenedioxyphenyl)-2-aminopropane

BRANNON
1-(2-methoxy-3,4-methylenedioxyphenyl)-2-methylaminopropane

CHRISTINA
1-(2-methoxy-3,4-methylenedioxyphenyl)-2-ethylaminopropane

"It's Just A New Way Of Thinking." - Wu-Tang [1997]

 

[Didgital]

OBOVATOLAMINE
1-(2-aminoprop-1-yl)-3,4-methylenedioxy-5-((2-aminopropyl)phenoxy)benzene

From Obovatol, A Constituent Of Magnolia Tree Essential Oil.

"We From The Magnolia." - Juvenile ('of or like Jupiter'), 400 Degreez.

Stick an alkene between the methoxy group of MMDA and amphetamine and i could see some cleavage going on in stomach acids. However if it was a prodrug, you would get way fucked up on the amphetamine component way before the MMDA even makes an appearance.

 

[Didgital]

Tryptamine + CH3I --> LAH --> DMT

5-MeO-Tryptamine + CH3I --> LAH --> 5-MeO-DMT

Make Me!

Terrible idea. Methyl iodide and lithium aluminum hydride are both chemicals that are extremely hazardous.

Why not use NaBH4 and formaldehyde like the rest of the world.

 

[4DQSAR]

Terrible idea. Methyl iodide and lithium aluminum hydride are both chemicals that are extremely hazardous.

Why not use NaBH4 and formaldehyde like the rest of the world.

Besides that - you don't get the product you want. You get mixtures including the quaternary ammonium compounds.

But there is a name-reaction that under the correct conditions, gives almost quantitative yields. Note I have named neither the reaction nor the conditions - so anyone who understands it ALREADY KNEW.

 

[Smyth2]

^I think he means the Eschweiler–Clarke methylation.

Check this compound: AW-15'1129.

Can't seem to get this reference though: B. Roth, J. Faber and S. Nevs̈imalova, Activ. Nerv. Super., 14, 35 (1972).

 

[4DQSAR]

Well, compounds plural.

IF homologues in which that p-Cl can be substituted for , say, a thiomethyl or ethynyl are known, those might be more interesting.

I assume one enantiomer is the active or at least far more potent so this is an example of evergreening.

 

[Smyth2]

It's a cyclic aminal though so i'd expect that racemization occurs.

 

[4DQSAR]

It has a both a secondary and tertiary amine just one methylene from a bulky, lipophilic aromatic ring.

So using those old-school rules on choosing a chiral ligand to resolve enantiomers, it's not hard to choose a chiral diacid although I would always think about camphor-10-sulfonic acid because you are going to wind up with a salt that crashes right out...

But what you choose for bench-scale synthesis isn't really important. Yeild need only be 'enough' whereas any chemical engineer will really work to find the cheapest resolution. I see that the route given wouldn't allow the resolution of the precursor.

BTW assuming that slow onset and long DOA were design goals, the p-Me homologue would be the obvious one to test the scaffold. If nothing else, that methyl is nigh on perfect if you want to keep the ADME simple. I term such groups as 'sacrificial moieties' on the basis that they serve two purposes. They are required for the saught activity but also act as a labile moiety so you KNOW it will just be oxidized and gluconated.

 

[Rectify]

TRIPNOTIC

I Design Molecules, Not Synthetic Procedures.

And This One, Ladies & Gentlemen, Looks Like A Winner.