DALT

DALT
Clinical data
Other names	N,N-Diallyltryptamine; DALT; DAT
Routes of; administration	Oral, intramuscular injection
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A; US: Analogue to a Schedule I/II drug (possibly); UN: Unscheduled but not approved for human consumption.; in theory could be covered under similar analogue bills in other countries but this is not confirmed.;
Identifiers
	IUPAC name N-Allyl-N-[2-(1H-indol-3-yl)ethyl]prop-2-en-1-amine;
CAS Number	60676-77-9;
PubChem CID	24839550;
ChemSpider	21250454 ;
UNII	85113MO9BC;
CompTox Dashboard (EPA)	DTXSID001024249 ;
Chemical and physical data
Formula	C16H20N2
Molar mass	240.350 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C=CCN(CC=C)CCc2c[nH]c1ccccc12;
	InChI InChI=1S/C16H20N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h3-8,13,17H,1-2,9-12H2 ; Key:LQEATNFJCMVKAC-UHFFFAOYSA-N ;
	(verify)

N,N-Diallyltryptamine (DALT) is a tryptamine derivative which has been identified as a new psychoactive substance.^[2]^[3] It has been used as an intermediate in the preparation of radiolabeled diethyltryptamine.^[4]

Use and effects

According to Alexander Shulgin in TiHKAL, the dosage of DALT is >40 mg orally and its duration is unknown.^[1] Its effects have not been described.^[1] According to Stephen Szara and colleagues however, DALT and other extended N,N-dialkyltryptamines produce similar effects to dimethyltryptamine (DMT) but are longer-lasting, with durations of up to 3 hours.^[1]^[5]^[6]

Pharmacology

DALT activities
Target	Affinity (K_i, nM)
5-HT_1A	100
5-HT_1B	>10,000
5-HT_1D	689
5-HT_1E	378
5-HT_1F	ND
5-HT_2A	701
5-HT_2B	61
5-HT_2C	385
5-HT₃	>10,000
5-HT₄	ND
5-HT_5A	>10,000
5-HT₆	1,718
5-HT₇	>10,000
α_1A	1,663
α_1B	1,369
α_1D	>10,000
α_2A	124
α_2B	305
α_2C	901
β₁–β₃	>10,000
D₁, D₂	>10,000
D₃	672
D₄, D₅	>10,000
H₁	127
H₂–H₄	>10,000
M₁–M₅	>10,000
I₁	ND
σ₁	101 (rat)
σ₂	356 (rat)
TAAR1Tooltip Trace amine-associated receptor 1	ND
MORTooltip μ-Opioid receptor, DORTooltip δ-Opioid receptor	>10,000
KORTooltip κ-Opioid receptor	2,477
SERTTooltip Serotonin transporter	150 (K_i)
NETTooltip Norepinephrine transporter	1,121 (K_i)
DATTooltip Dopamine transporter	1,406 (K_i)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:^[7]^[8]^[9]^[10]

The receptor interactions of DALT have been studied.^[7]^[8]^[9]^[10] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[11]

History

DALT was first described in the scientific literature by Stephen Szara and colleagues by 1962.^[5]^[6]

References

^ ^a ^b ^c ^d Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
^ Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH (October 2015). "Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MSn, and LC-HR-MS-MS" (PDF). Analytical and Bioanalytical Chemistry. 407 (25): 7831–42. doi:10.1007/s00216-015-8955-0. PMID 26297461. S2CID 26086597.
^ Michely JA, Brandt SD, Meyer MR, Maurer HH (February 2017). "n, and LC-HR-MS/MS" (PDF). Analytical and Bioanalytical Chemistry. 409 (6): 1681–1695. doi:10.1007/s00216-016-0117-5. PMID 27933361. S2CID 206920201.
^ Brandt SD, Tirunarayanapuram SS, Freeman S, Dempster N, Barker SA, Daley PF, et al. (2008). "Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines". Journal of Labelled Compounds and Radiopharmaceuticals. 51 (14): 423–429. doi:10.1002/jlcr.1557.
^ ^a ^b Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.
^ ^a ^b Szara S, Hearst E (1962). "The 6-Hydroxylation of Tryptamine Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences. 96 (1): 134–141. Bibcode:1962NYASA..96..134S. doi:10.1111/j.1749-6632.1962.tb50108.x. The dipropyl and diallyl derivatives have similar hallucinogenic activity in man, as we found recently.
^ ^a ^b "Kᵢ Database". PDSP. 28 March 2025. Retrieved 28 March 2025.
^ ^a ^b Liu T. "BindingDB BDBM50140058 CHEMBL3752576". BindingDB. Retrieved 28 March 2025.
^ ^a ^b Cozzi NV, Daley PF (February 2016). "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines" (PDF). Bioorganic & Medicinal Chemistry Letters. 26 (3): 959–964. doi:10.1016/j.bmcl.2015.12.053. PMID 26739781.
^ ^a ^b Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs" (PDF). Neuropharmacology. 142: 231–239. doi:10.1016/j.neuropharm.2018.02.028. PMC 6230509. PMID 29499272.
^ Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. Vol. 36. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMC 5787039. PMID 28224459. The HTR has also been observed in rodents treated with N-methyl-N-ethyltryptamine (MET), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-diisopropyltryptamine (DIPT), and N,N-diallyltryptamine (DALT) (Fantegrossi et al. 2008; Smith et al. 2014; Carbonaro et al. 2015; Halberstadt and Klein, unpublished observations).

External links

[TiHKAL-1] Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.

[pmid26297461-2] Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH (October 2015). "Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MSn, and LC-HR-MS-MS" (PDF). Analytical and Bioanalytical Chemistry. 407 (25): 7831–42. doi:10.1007/s00216-015-8955-0. PMID 26297461. S2CID 26086597.

[pmid27933361-3] Michely JA, Brandt SD, Meyer MR, Maurer HH (February 2017). "n, and LC-HR-MS/MS" (PDF). Analytical and Bioanalytical Chemistry. 409 (6): 1681–1695. doi:10.1007/s00216-016-0117-5. PMID 27933361. S2CID 206920201.

[4] Brandt SD, Tirunarayanapuram SS, Freeman S, Dempster N, Barker SA, Daley PF, et al. (2008). "Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines". Journal of Labelled Compounds and Radiopharmaceuticals. 51 (14): 423–429. doi:10.1002/jlcr.1557.

[BrimblecombePinder1975-5] Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.

[SzaraHearst1962-6] Szara S, Hearst E (1962). "The 6-Hydroxylation of Tryptamine Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences. 96 (1): 134–141. Bibcode:1962NYASA..96..134S. doi:10.1111/j.1749-6632.1962.tb50108.x. The dipropyl and diallyl derivatives have similar hallucinogenic activity in man, as we found recently.

[PDSPKiDatabase-7] "Kᵢ Database". PDSP. 28 March 2025. Retrieved 28 March 2025.

[BindingDB-8] Liu T. "BindingDB BDBM50140058 CHEMBL3752576". BindingDB. Retrieved 28 March 2025.

[CozziDaley2016-9] Cozzi NV, Daley PF (February 2016). "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines" (PDF). Bioorganic & Medicinal Chemistry Letters. 26 (3): 959–964. doi:10.1016/j.bmcl.2015.12.053. PMID 26739781.

[KleinCozziDaley2018-10] Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs" (PDF). Neuropharmacology. 142: 231–239. doi:10.1016/j.neuropharm.2018.02.028. PMC 6230509. PMID 29499272.

[HalberstadtGeyer2018-11] Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. Vol. 36. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMC 5787039. PMID 28224459. The HTR has also been observed in rodents treated with N-methyl-N-ethyltryptamine (MET), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-diisopropyltryptamine (DIPT), and N,N-diallyltryptamine (DALT) (Fantegrossi et al. 2008; Smith et al. 2014; Carbonaro et al. 2015; Halberstadt and Klein, unpublished observations).

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