^abcdefghTrachsel D, Lehmann D, Enzensperger C (2013).Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. p. 866.ISBN978-3-03788-700-4.OCLC858805226. Retrieved31 January 2025.Die Tetrahydroisochinolin-THIQ)-Analoga 437 und 438 wurden als rigide Analoga von DOM (8) und DOB (2) untersucht. Sie waren jeweils deutlich weniger affin zum 5-HT Rezeptor als ihre Analoga [1821. Weiter vermochten sie in einer Diskriminationsstudie keinen Stimulus in DOM-trainierten Ratten zu erzeugen. [...] 437 Ki, h5-HT2A: 2150nM ([3H]Ketanserin) (Ki DOM: 100nM) [...] 438 Ki h5-HT2A: 242nM ([3H]Ketanserin) (Ki DOB: 41 nM)
^abcdeGlennon RA, Young R (5 August 2011). "Role of Stereochemistry in Drug Discrimination Studies".Drug Discrimination. Wiley. pp. 129–161.doi:10.1002/9781118023150.ch4.ISBN978-0-470-43352-2. Retrieved22 May 2025.Figure 4-13. Chemical structures of TDIQ, and conformationally constrained forms of amphetamine (AMPH-CR), methamphetamine (METH-CR), and the hallucinogens DOM (DOM-CR) and DOB (DOB-CR). [...] Conformationally constrained analogs of the hallucinogens DOM and DOB (i.e., DOM-CR and DOB-CR) were not recognized by rats trained to discriminate 1.0 mg/kg of DOM from saline vehicle, but substituted in rats trained to discriminate TDIQ from vehicle (ED50 = 4.2 and 3.4 mg/kg, respectively) [15]. Interestingly, the TDIQ stimulus did not generalize to the N-methyl analog of DOM-CR [15]. Taken together with the findings obtained for METH-CR, it would appear that N-methylation is not tolerated with regard to producing TDIQ-like discriminative stimulus effects [15]. But, more importantly, and to reiterate what was stated above, it should not be assumed that "inactive" conformationally constrained rotamers are necessarily pharmacologically inactive; results depend on the similarity in the stimulus properties of the training drug and test agent.
^abcdefghMalmusi L, Dukat M, Young R, Teitler M, Darmani NA, Ahmad B, et al. (January 1996). "1,2,3,4-Tetrahydroisoquinoline analogs of phenylalkylamine stimulants and hallucinogens".Medicinal Chemistry Research.6 (6):400–411.Conformationally constrained, 1,2,3,4-tetrahydroisoquinoline (TIQ) analogs of central stimulant (e.g. amphetamine) and hallucinogenic (e.g. DOM) phenylalkylamines were prepared and evaluated to determine the contribution to activity of this conformational restriction. The amphetamine-related TIQs failed to produce locomotor stimulation in mice and did not produce amphetamine-appropriate responding in tests of stimulus generalization in (+)amphetamine-trained rats. Hallucinogen-related TIQs lacked appreciable affinity for 5-HT2A serotonin receptors and did not produce DOM-like effects in tests of stimulus generalization in DOM-trained rats. It is concluded that the phenylalkylamine conformation represented by the TIQs is not a major contributor to these actions.
^abcdefGlennon RA, Young R, Rangisetty JB (May 2002). "Further characterization of the stimulus properties of 5,6,7,8-tetrahydro-1,3-dioxolo[4,5-g]isoquinoline".Pharmacology, Biochemistry, and Behavior.72 (1–2):379–387.doi:10.1016/s0091-3057(01)00768-7.PMID11900809.
