DOB-CR

DOB-CR, or DOB/CR, , an acronym of "DOB-conformationally restrained", also known as 7-bromo-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline, is a serotonin receptor modulator of the tetrahydroisoquinoline family.^[1][2][3][4] It is a cyclized phenethylamine and a derivative of the psychedelic drugs 2C-B and DOB in which the side chain has been cyclized with the benzene ring to form a tetrahydroisoquinoline (THIQ) ring system.^[1][2][4][3]

DOB-CR

Clinical data
Other names	DOB/CR; "DOB-Conformationally Restrained"; 5,8-Dimethoxy-7-bromo-THIQ; 7-Bromo-5,8-dimethoxy-THIQ; DOB-THIQ; DOB/THIQ
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name 7-bromo-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline
CAS Number	183429-24-5
PubChem CID	9838353
ChemSpider	8014073
Chemical and physical data
Formula	C11H14BrNO2
Molar mass	272.142 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C2=C1CCNC2)OC)Br
InChI InChI=1S/C11H14BrNO2/c1-14-10-5-9(12)11(15-2)8-6-13-4-3-7(8)10/h5,13H,3-4,6H2,1-2H3 Key:YDHKNGFINXQAKM-UHFFFAOYSA-N

Pharmacology

The drug shows modest affinity for the serotonin 5-HT_2A receptor.^[1][3] Its affinity (K_i) for the receptor was 242 to 250 nM, which is about 6-fold lower than that of DOB.^[1][3] In contrast to DOB, DOB-CR completely failed to substitute for DOM in rodent drug discrimination tests.^[1][2][3][4] In addition, behavioral disruption occurred at higher doses.^[1][3] These findings suggest that DOB-CR would lack psychedelic effects in humans.^[1][2][3][4] The drug also failed to substitute for dextroamphetamine and MDMA in rodent drug discrimination tests, suggesting lack of stimulant or entactogenic effects as well.^[4] However, DOB-CR fully substituted for the structurally related selective α₂-adrenergic receptor ligand TDIQ (MDTHIQ or MDA-CR), albeit with about 4-fold lower potency than TDIQ itself.^[2][4]

History

DOB-CR was first described in the scientific literature by Richard Glennon and colleagues by 1996.^[1][3]

See also

• Substituted tetrahydroisoquinoline
• Cyclized phenethylamine
• DOM-CR
• TDIQ (MDTHIQ or MDA-CR)
• Tetrahydroisoquinoline (THIQ; AMPH-CR)