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Rectify's molecular poetry thread

2-amino-1-oxo-1-phenylpropane.png


CAT
(+)-2-amino-1-oxo-1-phenylpropane

The Wolff-Kishner

2-amino-1-phenylpropane.png


(+)-AMP
2-amino-1-phenylpropane

Make Me!

PHI_FI_PHO_FUM
I Smell The Blood Of An Englishmun.
 
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N,N-diethyl-1-phenyl-1-carbomethoxy-2-amino-propane.png


ELON_NOEL_LEON
N,N-diethyl-1-phenyl-1-carbomethoxy-2-amino-propane
 
Anisole.png


ANISOLE
1-methoxybenzene

1-methoxy-4-(1-oxopropyl)-benzene.png


1-methoxy-4-(1-oxo-2-bromopropyl)-benzene.png


1-methoxy-4-(1-oxo-2-methylamino-propyl)-benzene.png


1-methoxy-4-(1-hydroxy-2-methylamino-propyl)-benzene.png


The Williamson Ether Synthesis.

1-methoxy-4-(1-methoxy-2-methylamino-propyl)-benzene.png


CLOUD_9
1-methoxy-4-(1-methoxy-2-methylamino-propyl)-benzene

The Sign Says, "Proceed With Caution."
 
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indole.png


INDOLE

3-(1-oxopropyl)-indole.png


3-(1-oxo-2-bromopropyl)-indole.png


Protect carbonyl with ethylene glycol (antifreeze) and OH- to yield a spiro 1,3-dioxacyclopently functional group, then swap R-Br for R-NHCH3 and then finally deprotect with H+. The protecting group may only be necessary for certain primary R-NH2 containing compounds. I really don't know about that for certain.

3-(1-oxo-2-methylaminopropyl)-indole.png


DAVE'S_KILLER_BREAD
3-(1-oxo-2-methylaminopropyl)-indole

Some Of The Best Bread Around!
 
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1-phenyl-1-carboxy-2-methylaminopropane.png


CH3CH2OH, HCl, reflux

1-phenyl-1-carboethoxy-2-methylaminopropane.png


ERASTOTHENES
1-phenyl-1-carboethoxy-2-methylaminopropane
 
3,4-dichlorobenzaldehyde.png


3,4-dichlorobenzaldehyde

1-(2-nitro-prop-1-ene-yl)-3,4-dichlorobenzene.png


1-(2-oxopropyl)-3,4-dichlorobenzene.png


1 molar equivalent of Br2(liquid).

1-(2-oxo-1-bromopropyl)-3,4-dichlorobenzene.png


Reductive Amination

1-(2-methylamino-1-bromopropyl)-3,4-dichlorobenzene.png


1-(2-methylamino-1-cyanopropyl)-3,4-dichlorobenzene.png


1-(2-methylamino-1-carboxypropyl)-3,4-dichlorobenzene.png


1-(2-methylamino-1-carboethoxypropyl)-3,4-dichlorobenzene.png


SiiiCK!
1-(2-methylamino-1-carboethoxypropyl)-3,4-dichlorobenzene
 
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N-(1-oxopropyl)-aniline.png


NON-NARCOTIC_TYLESET
N-(1-oxopropyl)-aniline

N-(1-oxopropyl)-N-(1-methyl-2-phenylethyl)-aniline.png


NARCOTIC_TYLENAMP; CII.
N-(1-oxopropyl)-N-(1-methyl-2-phenylethyl)-aniline
 
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aniline.png


ANILINE
1-aminobenzene

1-phenyl-2-oxopropane.png

1-phenyl-2-oxopropane

N-phenyl-2-phenyl-1-methylethylamine.png

N-phenyl-2-phenyl-1-methylethylamine

1-chloro-1-oxopropane.png

1-chloro-1-oxopropane

N-(1-oxopropyl)-N-(1-methyl-2-phenylethyl)-aniline.png


NARCOTIC_TYLENAMP; CII.
N-(1-oxopropyl)-N-(1-methyl-2-phenylethyl)-aniline

EZ Does It!
 
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aniline.png


ANILINE
1-aminobenzene

1-chloro-1-oxopropane.png

1-chloro-1-oxopropane

N-(1-oxopropyl)-aniline.png


NON-NARCOTIC_TYLESET
N-(1-oxopropyl)-aniline

Non Steroidal Anti Inflammatory Drug (NSAID).
 
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1280px-C%E2%80%901027_chromophore.svg.png

This isn't anything I came up with. It is a chemotherapeutic drug called lidamycin.

It causes double strand breaks in DNA from that central enediyene ring rearranging into a phenyl ring, which forms an extremely reactive benzenoid diradical, which cleaves both strands of DNA (a Bergman cyclization).

Mechanism below

1280px-C-1027_mechanism.png


This class of compounds is extremely potent, killing cultured cancer cells in low picomolar quantities.

This is impressive to me, because most things this toxic are catalysts; that is, they exert their damage in a cycle, that regenerates the damaging potential. Heavy metals for example can just repeatedly grab electrons and then give them away to water molecules, creating reactive oxygen species that damage biomolecules. Similar are enzymatic toxins like ricin, that slice off one RNA base on a ribosome, disabling them from translating proteins.

These enediyenes are different. They are stoichiometric toxins. The majority of toxins are like this, where their toxicity comes from the formation of a chemical bond that breaks something inside of a cell. Cyanide binds iron in blood cells and mitochondria so makes you unable to make ATP. Organophosphates bind to acetylcholinesterase and prevent acetylcholine hydrolysis. Alkylating agents like mustard gas simply react with proteins that have nucleophilic hot spots, like the sulfur in cystienes.

The enediyene ring opening can only occur once, so at best one molecule of lidamycin could cut one duplex of DNA.

To have such a high potency (think three orders of magnitude more potent than common chemotherapeutics) while not being catalytic (or doing something like activating a hormone receptor potently like dioxin) boggles my mind.
 
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N-phenyl-N-(4-methoxyphenyl)-N-(3,4-methylenedioxyphenyl)amine.png


HAPPY_FAMILY
N-phenyl-N-(4-methoxyphenyl)-N-(3,4-methylenedioxyphenyl)amine
 
(6aR,10aR)-6,6,9-Trimethyl-1-methoxy-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo%5bc%5dchromen.png


THC-M
(6aR,10aR)-6,6,9-trimethyl-1-methoxy-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzochromene
 
1-phenyl-1-carbomethoxy-2-methylaminopropane.png


SATISFECHO
1-phenyl-1-carbomethoxy-2-methylaminopropane

1-(3,4-methylenedioxyphenyl)-1-carbomethoxy-2-methylaminopropane.png


MUY_SATISFECHO
1-(3,4-methylenedioxyphenyl)-1-carbomethoxy-2-methylaminopropane

Just Can't Figure Out How The 2nd One Would Be Made. Also_Tapered?

A Penny For Your Thoughts?
 
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I've often wondered if this DMT intermediate would do anything on its own?

1-(indole-3-yl)-1,2-dioxo-2-dimethylaminoethane.png
 
1-(2-amino-3,4,5-trimethoxyphenyl)-2-aminoethane.png


YANA
1-(2-amino-3,4,5-trimethoxyphenyl)-2-aminoethane

A Higher Love.
 
(6aR,9R)-N,N-diethyl-7-(1-methyl2-phenylethyl)-4,6,6a,7,8,9-hexahydroindolo-%5b4,3-fg%5d-quinoline-9-carboxamide.png


LSD-AMP
(6aR,9R)-N,N-diethyl-7-(1-methyl-2-phenylethyl)-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]-quinoline-9-carboxamide

(6aR,9R)-N,N-diethyl-7-(1-methyl-2-(3,4-methylenedioxyphenyl)ethyl)-4,6,6a,7,8,9-hexahydroindolo-%5b4,3-fg%5d-quinoline-9-carboxamide.png


LSD-X
(6aR,9R)-N,N-diethyl-7-(1-methyl-2-(3,4-methylenedioxyphenyl)ethyl)-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]-quinoline-9-carboxamide

from nor-LSD
 
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chemrxiv.org

Synthesis of N–H Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids as Aminating Agent

Herein, we presented a practical methodology for the intermolecular aziridination of alkenes, using HOSA as the aminating agent, alongside pyridine or piperidine as the base, within HFIP solvent system. Notably, this approach showcases excellent reactivity, especially with non-activated alkenes...
chemrxiv.org chemrxiv.org

I'm thinking once you have the N-H aziridine from the arene precursor, it could be opened somehow.
 
(6aR,9R)-N,N-diethyl-7-(1-phenyl-1-cyclohexyl)-4,6,6a,7,8,9-hexahydroindolo-%5b4,3-fg%5d-quinoline-9-carboxamide.png


THE_INCREDIBLE_HULK
(6aR,9R)-N,N-diethyl-7-(1-phenyl-1-cyclohexyl)-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]-quinoline-9-carboxamide
 
(6aR,9R)-N,N-diethyl-7-(trifluoromethyl)-4,6,6a,7,8,9-hexahydroindolo-%5b4,3-fg%5d-quinoline-9-carboxamide.png


N-TFM-LSD
(6aR,9R)-N,N-diethyl-7-(trifluoromethyl)-4,6,6a,7,8,9-hexahydroindolo-%5b4,3-fg%5d-quinoline-9-carboxamide

1-phenyl-2-(trifluoromethylamino)-propane.png


N-TFM-AMP
1-phenyl-2-(trifluoromethylamino)-propane

1-(3,4-methylenedioxyphenyl)-2-(trifluoromethylamino)-propane.png



N-TFM-MDA
1-(3,4-methylenedioxyphenyl)-2-(trifluoromethylamino)-propane
 
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