Deinonychus
Bluelighter
- Joined
- Oct 20, 2012
- Messages
- 402
Hi guys! So a thread popped up in PD about how this fellow got something that was active at the level of 100 micrograms but which was supposedly neither LSD nor AL-LAD. He wanted help identifying it, which will be futile for the obvious reasons, but it brought something to mind. I noticed this compound in a paper a month or two ago and I've been meaning to post about it here in ADD since then, but kept putting it off. So I'm doing that belated posting now.
The compound in question is N,N-Diethyl-3-{[1-(4-iodo-2,5-dimethoxyphenyl)propan-2-yl]amino)propanamide. This substance had the highest binding affinity at 5-HT2a of any agonist or partial agonist in the paper I read, though they left LSD and the N-benzyl PEAs out. Still, it looks like it's got a rather high binding affinity, and has a curious structure, so I wonder what you all think of it from the perspective of SAR. Yeah, high affinity at 5-HT2a isn't the sole criterion for a possibly cool psychedelic (ie a high affinity for a different subtype may lead to the Phenfen cardiovascular problems, or anxiety, or whatever, possibly negating any value as a paychedelic derived from its action on the 2a subtype) but it certainly is pretty much required. I don't know much about SAR beyond the obvious stuff, like 4-position substituents on vanilla PEAs or alkyl substituents on the aliphatic amine of a tryptamine, so I figured I'd bring the compound to your attention if it hasn't already become known to you.
It looks like this:
Ki of 3.2 nM, compared to 2.5 nM for LSD, which wasn't one of the substances studied in the paper (this compound I'm posting about had the greatest affinity of the compounds they did include in the study).
The paper is: 'Quasi-atomistic Surrogates for the 5-HT2a Receptor: a 3D-QSAR Study onHallucinogenic Substances', it's available on bitnest. I'm pretty sure all the days was derived in silico. Curiously the iodine substituted form beat out the chlorinated and brominated versions, at least in the computer. The researchers describe it as a hybrid structure between PEAs and LSD, I definitely see where they're coming from there although that's a slight exaggeration considering how complex the structure of LSD is in comparison to this compound, as slapping a diethylamide moiety onto an ethyl and attaching all that to the amine of a PEA doesn't constitute a new chemical that's 'half and half' like a first-generation hybrid. Honestly this looks to me like a doodle I would do for the fun but silly reason of taking the diethylamide from acid and putting it into a PEA, like it belongs in the 'drawing random molecules' thread. Makes one wonder about replacing the diethylamide with a dimethylazetidide, a la LSZ. Surely the SAR isn't that directly analogous?
So, does this perhaps look intriguing? Again I don't know enough about SAR when it comes to compounds that are reasonably different from their relatives, which this definitely qualifies as, so if anybody has any insights they'd be interested to share that would be great.
That's all!
The compound in question is N,N-Diethyl-3-{[1-(4-iodo-2,5-dimethoxyphenyl)propan-2-yl]amino)propanamide. This substance had the highest binding affinity at 5-HT2a of any agonist or partial agonist in the paper I read, though they left LSD and the N-benzyl PEAs out. Still, it looks like it's got a rather high binding affinity, and has a curious structure, so I wonder what you all think of it from the perspective of SAR. Yeah, high affinity at 5-HT2a isn't the sole criterion for a possibly cool psychedelic (ie a high affinity for a different subtype may lead to the Phenfen cardiovascular problems, or anxiety, or whatever, possibly negating any value as a paychedelic derived from its action on the 2a subtype) but it certainly is pretty much required. I don't know much about SAR beyond the obvious stuff, like 4-position substituents on vanilla PEAs or alkyl substituents on the aliphatic amine of a tryptamine, so I figured I'd bring the compound to your attention if it hasn't already become known to you.
It looks like this:
Ki of 3.2 nM, compared to 2.5 nM for LSD, which wasn't one of the substances studied in the paper (this compound I'm posting about had the greatest affinity of the compounds they did include in the study).
The paper is: 'Quasi-atomistic Surrogates for the 5-HT2a Receptor: a 3D-QSAR Study onHallucinogenic Substances', it's available on bitnest. I'm pretty sure all the days was derived in silico. Curiously the iodine substituted form beat out the chlorinated and brominated versions, at least in the computer. The researchers describe it as a hybrid structure between PEAs and LSD, I definitely see where they're coming from there although that's a slight exaggeration considering how complex the structure of LSD is in comparison to this compound, as slapping a diethylamide moiety onto an ethyl and attaching all that to the amine of a PEA doesn't constitute a new chemical that's 'half and half' like a first-generation hybrid. Honestly this looks to me like a doodle I would do for the fun but silly reason of taking the diethylamide from acid and putting it into a PEA, like it belongs in the 'drawing random molecules' thread. Makes one wonder about replacing the diethylamide with a dimethylazetidide, a la LSZ. Surely the SAR isn't that directly analogous?
So, does this perhaps look intriguing? Again I don't know enough about SAR when it comes to compounds that are reasonably different from their relatives, which this definitely qualifies as, so if anybody has any insights they'd be interested to share that would be great.
That's all!