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I Like to Draw Pictures of Random Molecules

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^ In fact, morphinelike compounds need to have the phenolic 3-hydroxy group or they lose potency completely... (thats why codeine or heroin isn't active before it's hydrolyzed in the body) You should connect that tropane part only to the cyclohexene ring.

EDIT: I was talking about the first molecule, where theres a carboxyl at 3-position.
 
polymath said:
^ In fact, morphinelike compounds need to have the phenolic 3-hydroxy group or they lose potency completely... (thats why codeine or heroin isn't active before it's hydrolyzed in the body) You should connect that tropane part only to the cyclohexene ring.

EDIT: I was talking about the first molecule, where theres a carboxyl at 3-position.
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Yes, which was why I was wondering how it would metabolize, or if the cocaine part would even be active: I'd like the morphine to come on after the other metabolizes for obvious reasons ;-)

I call this one 'MK Ultra' (:-p):

MKUltra.jpg


Wonder if it'd be more viable somewhere on a PCP ring.
 
If that carbonyl is put to 4-position instead of 2-position on the cyclohexane ring, the compound becomes an opiate AFAIK. (use the search function and look for 4-oxo-PCP) I'm not sure if theres a way to make a drug that's both a strong opiate and a strong dissociative...
 
http://www.bluelight.ru/vb/threads/504286-PCP-analogs-(Cumulative)

4-phenyl-4-(piperidin-1-yl)cyclohexanone, 4-Oxo-PCP

Route/dose: 20mg intramuscularly of HCl salt
Report:
This is an interesting compound. It almost completely lost its NMDA blockade effects. Instead it possesses opioid-like activity. Probably PCE analogs of this would yield very strong narcotic-like compounds. But that's just a prediction. PCE analog could still retain NMDA antagonist properties while having strong a narcotic effect similar to that of morphine.
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Also look for the "Synthesis and effects of PCP analogs" article in Rhodium's drug chemistry archive at Erowid (I can't give a link because there's drug synth discussion there). There's good basic info about arylcyclohexylamine's SAR and the 4-oxo compounds are also mentioned there:

Ketamine (1-(2-chlorophenyl)-1-methylamino-(2-cyclohexanone) has a carbonyl substituent at the two-position of the cyclohexane ring. This confers the desirable property of increasing elimination and decreasing the duration of anesthetic action, and may enhancie the analgesic potency. The veterinary anesthetic tiletamine (the N-ethyl 2-thienyl analog of Ketamine) also has a carbonyl group at the same position.

If the carbonyl group is moved to the 4-position of the cyclohexane ring, compounds that are active analgesics comparable to morphine can result, along with a reduction in PCP-like activity.
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Weren't you looking for a compound that's both mu agonist and NMDA antagonist in another thread?
 
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3'-OH PCP is a known opioid arylcyclohexylamine (the exp. report notes unconciousness at sub-10mg doses(!!!)), so is bromidol if you want to go that far into left field.

I think your best bet for the Holy Trinity of receptor site occupancy would be a derivative of 3'-OH-PCE. 3' acetyl PCE anyone? Though it does depend on the ratio of effects desired from all 3 sites - you may want to look into meperidine analogs.
 
What is it called when you change a ketone to an aldehyde, sorry can't use my chem sketch as am a retard. So say with amphetamine, MDMA etc if in stead of putting a ketone in to make a cathone you put an extra carbon coming off where the ketone would (double bonded) and then a double bonded oxygen?

Or what about it you changed the cathone to an ether bond? would it just break up
 
lgaWV.png

Aldehydes are reactive and will react with amines to form imines (Schiff bases) and water. That's why you don't see beta-carbonyl amphetamine.

The CH2->O version of amphetamine is 1-aminoethanol phenyl ether. I don't know if it would be active.
 
sekio said:
lgaWV.png

Aldehydes are reactive and will react with amines to form imines (Schiff bases) and water. That's why you don't see beta-carbonyl amphetamine.

The CH2->O version of amphetamine is 1-aminoethanol phenyl ether. I don't know if it would be active.
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Thanks for your reply :)
 
{1-aminoethanol phenyl ether structure}
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No that molecule is UNstable and would cleave back to a phenol, acetaldehyde and ammonia. You do not even need any special conditions in decomposing it apart from "room temp". (or even -78C). Take note at the "aminal" structure and its properties. (not animal xD)
 
mr shush said:
What is it called when you change a ketone to an aldehyde, sorry can't use my chem sketch as am a retard. So say with amphetamine, MDMA etc if in stead of putting a ketone in to make a cathone you put an extra carbon coming off where the ketone would (double bonded) and then a double bonded oxygen?

Or what about it you changed the cathone to an ether bond? would it just break up
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What about methyl ester of 2-phenyl-3-aminobutanoic acid? That would be like an open-chain version of methylphenidate.
 
mr shush said:
What is it called when you change a ketone to an aldehyde
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I think you're referring to reduction, but you can't change a ketone to an aldehyde, because an aldehyde is by definition at the end of a carbon chain, and a ketone is by definition in the middle of one (aldehydes and ketones also have the same oxidation state, which is a good clue that neither is accessible through oxidation/reduction of the other). Via reduction, aldehydes are made from carboxylic acids.
 
Roger&Me said:
I think you're referring to reduction, but you can't change a ketone to an aldehyde, because an aldehyde is by definition at the end of a carbon chain, and a ketone is by definition in the middle of one (aldehydes and ketones also have the same oxidation state, which is a good clue that neither is accessible through oxidation/reduction of the other). Via reduction, aldehydes are made from carboxylic acids.
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I think he was talking about inserting an intervening carbon, as if you somehow replaced the carbonyl with formaldehyde. If there is a reaction that does this, it's not undergrad-level chemistry.
 
Wittig reaction can do that, with the phosphonium salt made from MOM-Cl and a trialkylphosphine (I don't know if PPh3 is the best, and they don't work so well on ketones sometimes, so maybe there are better conditions) and is undergrad level.
 
I'd prefer taking this:
dioxygendiyl ,the ground state of molecular oxygen. bearing DOUBLE RADICAL form.

temp2.gif
 
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