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Dimethylhomotryptamine
Pharmaceutical compound From Wikipedia, the free encyclopedia
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Dimethylhomotryptamine (DMHT; developmental code name U-6056), also known as N,N-dimethylhomotryptamine or as 3-[3-(dimethylamino)propyl]indole, is a homotryptamine and homologue of the psychedelic tryptamine dimethyltryptamine (DMT) in which the alkyl side chain has been lengthened by one carbon atom.[1][2][3][4][5] The homologue of DMT in which the alkyl side chain has been shortened by one carbon atom is gramine (3-(N,N-dimethylaminomethyl)indole).[1]
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Use and effects
According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) and other publications, DMHT was studied by the Upjohn Company under the code name U-6056.[1][2][5] It was assessed in a clinical study of 10 individuals at doses of up to 10 mg by intravenous injection and 70 mg by intramuscular injection, but produced no psychoactive or hallucinogenic effects besides mild agitation or anxiety and caused slight increases in heart rate and blood pressure.[1][2][3][4][5] For comparison, DMT has been reported to produce psychedelic effects at doses as low as 20 to 50 mg by intramuscular injection.[1] The human properties and effects of the lower homologue gramine are unknown.[1]
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Pharmacology
Pharmacodynamics
DMHT showed the same affinity for serotonin receptors in the rat fundus strip as DMT (A2 = 1,000 nM and 1,000 nM, respectively).[6][7] It also shows low affinity for the serotonin 5-HT3 receptor (Ki = 730 nM).[8] The drug's analogue homotryptamine (the N,N-didesmethyl analogue) showed abolished affinity for the serotonin 5-HT1E and 5-HT1F receptors (Ki = >10,000 nM).[9] DMHT is a potent serotonin reuptake inhibitor (SRI), with an affinity (IC50) for the serotonin transporter (SERT) of 58 nM.[10] It produced hyperthermia in rabbits.[4][11][12][13]
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Chemistry
Synthesis
The chemical synthesis of DMHT has been described.[6]
Analogues
Other DMT and DMHT homologues with further extended alkyl chains have been studied, but were said to have no interesting activity.[4][13] The highly potent selective serotonin reuptake inhibitor (SSRI) BMS-505130 (Ki = 0.18 nM for the SERT) was derived via structural modification of DMHT.[14][15]
History
DMHT was first described in the scientific literature by William J. Turner and Sidney Merlis in 1959.[5]
See also
References
External links
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