DOM-CR

DOM-CR, or DOM/CR, an acronym of "DOM-conformationally restrained", is a tetrahydroisoquinoline (THIQ) and cyclized phenethylamine related to the psychedelics DOM and 2C-D.^[1][2][3] It is a cyclized THIQ analogue of DOM and 2C-D.^[1][2][3]

DOM-CR

Clinical data
Other names	DOM/CR; "DOM-Conformationally Restrained"; 5,8-Dimethoxy-7-methyl-THIQ; DOM-THIQ; DOM/THIQ
Identifiers
IUPAC name 5,8-dimethoxy-7-methyl-1,2,3,4-tetrahydroisoquinoline
CAS Number	228997-46-4
PubChem CID	10198181
ChemSpider	8373681
Chemical and physical data
Formula	C12H17NO2
Molar mass	207.273 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=C2CCNCC2=C1OC)OC
InChI InChI=1S/C12H17NO2/c1-8-6-11(14-2)9-4-5-13-7-10(9)12(8)15-3/h6,13H,4-5,7H2,1-3H3 Key:LDSXYNSFNYUAHP-UHFFFAOYSA-N

DOM-CR shows more than 20-fold reduced affinity for the serotonin 5-HT_2A receptor compared to DOM (K_i = 2,150 nM vs. 100 nM, respectively).^[3] In contrast to DOM, DOM-CR does not substitute for DOM in rodent drug discrimination tests, suggesting that it lacks psychedelic effects.^[1][2][3] Similarly, DOM-CR does not substitute for dextroamphetamine or MDMA, suggesting that it likewise lacks stimulant or entactogenic effects.^[2] However, DOM-CR does substitute for TDIQ (MDTHIQ), a selective α₂-adrenergic receptor ligand.^[1][2] At high doses, DOM-CR produces behavioral disruption in drug discrimination tests.^[2] In contrast to DOM and amphetamine, DOM-CR does not produce hyperlocomotion in rodents.^[3]

DOM-CR was first described in the scientific literature by Richard Glennon and colleagues by 1996.^[2][3]

Analogues

Other cyclized THIQ analogues of psychoactive phenethylamines have also been developed and characterized.^{[2][3][4][5][6]} 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.^{[2][3][4][5][6]} Conformational restriction of stimulant, 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 transporters and/or serotonin 5-HT₂ receptors.^[2][4] However, it does not necessarily remove all pharmacological activity, as evidenced by some THIQs interacting with α₂-adrenergic receptors^[2] as well as serotonin 5-HT_1D, 5-HT₆, and/or 5-HT₇ receptors^[2][7][8] and producing behavioral effects in animals.^[2]

Other cyclized analogues of DOM and related psychedelics include DOM-AT, DOM-AI, DMCPA, TFMBOX, jimscaline, TCB-2, LPH-5, and ZC-B.^[9][10][11]

See also

• Substituted tetrahydroisoquinoline
• Lorcaserin
• CT-5126