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Discriminative stimulus effects of N,N-diisopropyltryptamine

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Serotonergic hallucinogens such as (+)-lysergic acid diethylamide (LSD) and dimethyltryptamine (DMT) produce distinctive visual effects, whereas the synthetic hallucinogen N,N-diisopropyltryptamine (DiPT) is known for its production of auditory distortions.


This study compares the discriminative stimulus effects of DiPT to those of visual hallucinogens.


Adult male rats were trained to discriminate DiPT (5 mg/kg, 15 min) from saline under a FR10 schedule. A dose–effect and time course of DiPT's discriminative stimulus effects were established. DMT, (−)-2,5-dimethoxy-4-methylamphetamine (DOM), LSD, (±)-methylenedioxymethamphetamine (MDMA), and (+)-methamphetamine were tested for cross-substitution in DiPT-trained animals.


Rats learned to discriminate DiPT from saline in an average of 60 training sessions (30 drug and 30 saline). DiPT (0.5–5 mg/kg) produced dose-dependent increases in drug-appropriate responding (DAR) to 99 % (ED50 = 2.47 mg/kg). Onset of the discriminative stimulus effects was within 5 min, and the effects dissipated within 4 h. Full substitution for the discriminative stimulus effects of DiPT occurred with LSD, DOM, and MDMA. DMT only partially substituted for DiPT (65 % DAR), whereas (+)-methamphetamine failed to substitute for DiPT (29 % DAR).


The discriminative stimulus effects of DiPT were similar those of a number of synthetic hallucinogens, only partially similar to those of DMT, but not similar to (+)-methamphetamine. The putative DiPT-induced auditory distortions do not lead to discriminative stimulus effects distinguishable from other hallucinogens.

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  1. Appel JB, West WB, Rolandi WG, Alici T, Pechersky K (1999) Increasing the selectivity of drug discrimination procedures. Pharmacol Biochem Behav 64:353–358

    PubMed  Article  CAS  Google Scholar 

  2. Buckholtz NS, Boggan WO (1977) Monoamine oxidase inhibition in brain and liver produced by beta-carbolines: structure–activity relationships and substrate specificity. Biochem Pharmacol 26:1991–1996

    PubMed  Article  CAS  Google Scholar 

  3. Cozzi NV, Gopalakrishnan A, Anderson LL, Feih JT, Shulgin AT, Daley PF, Ruoho AE (2009) Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J Neural Transm 116:1591–1599

    PubMed  Article  CAS  Google Scholar 

  4. Gatch MB, Rutledge MA, Carbonaro T, Forster MJ (2009) Comparison of the discriminative stimulus effects of dimethyltryptamine with different classes of psychoactive compounds in rats. Psychopharmacology 204:715–724

    PubMed  Article  CAS  Google Scholar 

  5. Gatch MB, Forster MJ, Janowsky A, Eshleman AJ (2011) Abuse liability profile of three substituted tryptamines. J Pharmacol Exp Ther 338:280–289

    PubMed  Article  CAS  Google Scholar 

  6. Glennon RA (1986) Discriminative stimulus properties of phenylisopropylamine derivatives. Drug Alcohol Depend 17:119–134

    PubMed  Article  CAS  Google Scholar 

  7. Glennon RA (1988) Site-selective serotonin agonists as discriminative stimuli. Psychopharmacol Ser 4:15–31

    PubMed  CAS  Google Scholar 

  8. Glennon RA (1999) Arylalkylamine drugs of abuse: an overview of drug discrimination studies. Pharmacol Biochem Behav 64:251–256

    PubMed  Article  CAS  Google Scholar 

  9. Glennon RA, Young R, Jacyno JM, Slusher M, Rosecrans JA (1983) DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines. Eur J Pharmacol 86:453–459

    PubMed  Article  CAS  Google Scholar 

  10. Helsley S, Fiorella D, Rabin RA, Winter JC (1998) A comparison of N, N-dimethyltryptamine, harmaline, and selected congeners in rats trained with LSD as a discriminative stimulus. Prog Neuropsychopharmacol Biol Psychiatry 22:649–663

    PubMed  Article  CAS  Google Scholar 

  11. Jarbe TU (1980) LSD-25 as a discriminative stimulus for response selection by pigeons. Pharmacol Biochem Behav 13:549–554

    PubMed  Article  CAS  Google Scholar 

  12. Nagai F, Nonaka R, Satoh K, Kamimura H (2007) The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. Eur J Pharmacol 559:132–137

    PubMed  Article  CAS  Google Scholar 

  13. National Research Council (2003) Guidelines for the Care and Use of Mammals in Neuroscience and Behavioral Research. The National Academies, Washington (DC)

    Google Scholar 

  14. Nichols DE (2004) Hallucinogens. Pharmacol Ther 101:131–181

    PubMed  Article  CAS  Google Scholar 

  15. Pierce PA, Peroutka SJ (1989) Hallucinogenic drug interactions with neurotransmitter receptor binding sites in human cortex. Psychopharmacology 97:118–122

    PubMed  Article  CAS  Google Scholar 

  16. Shulgin AT, Carter MF (1980) N, N-Diisopropyltryptamine (DIPT) and 5-methoxy-N, N-diisopropyltryptamine (5-MeO-DIPT). Two orally active tryptamine analogs with CNS activity. Commun Psychopharmacol 4:363–369

    PubMed  CAS  Google Scholar 

  17. Shulgin AT, Shulgin A (1997) TiHKAL: The continuation. Transform, Berkeley

    Google Scholar 

  18. Strassman RJ, Qualls CR, Berg LM (1996) Differential tolerance to biological and subjective effects of four closely spaced doses of N, N-dimethyltryptamine in humans. Biol Psychiatry 39:784–795

    PubMed  Article  CAS  Google Scholar 

  19. Titeler M, Lyon RA, Glennon RA (1988) Radioligand binding evidence implicates the brain 5-HT2 receptor as a site of action for LSD and phenylisopropylamine hallucinogens. Psychopharmacology 94:213–216

    PubMed  Article  CAS  Google Scholar 

  20. Winter JC (2009) Hallucinogens as discriminative stimuli in animals: LSD, phenethylamines, and tryptamines. Psychopharmacology 203:251–263

    PubMed  Article  CAS  Google Scholar 

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Funding was provided by the Addiction Treatment Discovery Program of the National Institute on Drug Abuse (NIH N01DA-7-8872) and by T32 AG020494.

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There are no conflicts of interest.

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Correspondence to Michael B Gatch.

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Carbonaro, T.M., Forster, M.J. & Gatch, M.B. Discriminative stimulus effects of N,N-diisopropyltryptamine. Psychopharmacology 226, 241–246 (2013).

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  • N,N-Diisopropyltryptamine
  • Hallucinogens
  • Drug discrimination
  • Rat