DOM-CR, or DOM/CR, an acronym of "DOM-conformationally restrained", is a

tetrahydroisoquinoline Tetrahydroisoquinoline (TIQ or THIQ), also known as AMPH-CR, is an organic compound with the chemical formula C9H11N. Classified as a secondary amine, it is derived from isoquinoline by hydrogenation. It is a colorless viscous liquid that is mis ...

(THIQ) and

cyclized phenethylamine Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...

related to the

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

s DOM and

2C-D 2C-D, also known as 2C-M or as 2,5-dimethoxy-4-methylphenethylamine, is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, a ...

. It is a cyclized THIQ analogue of DOM and 2C-D. DOM-CR shows more than 20-fold reduced

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A receptor compared to DOM (K_i = 2,150nM vs. 100nM, respectively). In contrast to DOM, DOM-CR does not substitute for DOM in rodent

drug discrimination Drug discrimination (DD) is a technique in behavioral neuroscience used to evaluate the discriminative stimulus properties or interoceptive cues of psychoactive drugs. In drug discrimination, a subject is trained on a training drug, and then i ...

tests, suggesting that it lacks psychedelic effects. Similarly, DOM-CR does not substitute for

dextroamphetamine Dextroamphetamine (international nonproprietary name, INN: dexamfetamine) is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narc ...

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor Psychedelic drug, psychedelic properties. In studies, it has been used ...

, suggesting that it likewise lacks

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

entactogen Entactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observe ...

ic effects. However, DOM-CR does substitute for TDIQ (MDTHIQ), a selective α₂-adrenergic receptor

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

. At high doses, DOM-CR produces behavioral disruption in drug discrimination tests. In contrast to DOM and

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

, DOM-CR does not produce

hyperlocomotion Locomotor activity is a measure of animal behavior which is employed in scientific research. Hyperlocomotion, also known as locomotor hyperactivity, hyperactivity, or increased locomotor activity, is an effect of certain drugs in animals in whi ...

in rodents. DOM-CR was first described in the

scientific literature Scientific literature encompasses a vast body of academic papers that spans various disciplines within the natural and social sciences. It primarily consists of academic papers that present original empirical research and theoretical ...

by Richard Glennon and colleagues by 1996.

Analogues

Other cyclized THIQ analogues of

psychoactive A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

phenethylamines have also been developed and characterized. These include AMPH-CR (THIQ), METH-CR (''N''-methyl-THIQ), TDIQ (MDTHIQ, MDA-CR), TDMIQ (MDMTHIQ, MDMA-CR), ''N''-methyl-DOM-CR (Beatrice-CR), DOB-CR, and PMMA-CR. Conformational restriction of

, hallucinogen, and/or entactogen phenethylamines into THIQ analogues, like the preceding compounds, usually reduces or abolishes their associated effects as well as their affinities for

monoamine transporter Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...

s and/or

5-HT₂ receptors. However, it does not necessarily remove all pharmacological activity, as evidenced by some THIQs interacting with α₂-adrenergic receptors as well as serotonin 5-HT_1D, 5-HT₆, and/or 5-HT₇ receptors and producing behavioral effects in animals. Other cyclized analogues of DOM and related psychedelics include

DOM-AT DOM-AT, or DOMAT, also known as 5,8-dimethoxy-6-methyl-2-aminotetralin, is a cyclized phenethylamine and 2-aminotetralin related to the psychedelic substituted amphetamine, amphetamine DOM (drug), DOM. It is specifically the cyclized 2-aminotetra ...

DOM-AI DOM-AI, also known as 4,7-dimethoxy-5-methyl-2-aminoindane, is a putative serotonergic psychedelic of the 2-aminoindane group related to DOM. It is a cyclized phenethylamine and the cyclized 2-aminoindane analogue of DOM. The drug fully subst ...

, DMCPA, TFMBOX,

jimscaline Jimscaline (C-(4,5,6-trimethoxyindan-1-yl)methanamine) is a conformationally-restricted derivative of the cactus-derived hallucinogen mescaline, which was reported in 2006 by a team at Purdue University led by David E. Nichols. It acts as a po ...

TCB-2 TCB-2 is a hallucinogen discovered in 2006 by Thomas McLean working in the lab of David Nichols at Purdue University. It is a conformationally-restricted derivative of the phenethylamine 2C-B, also a hallucinogen, and acts as a potent agonis ...

, LPH-5, and ZC-B.

References

External links

DOM-CR - Isomer Design
{{Phenethylamines Methoxyphenethylamines Methyl compounds Serotonin receptor modulators Tetrahydroisoquinolines

Analogues

See also

References

External links