DALT

Diallyltryptamine (DALT), also known as N,N-diallyltryptamine, is a tryptamine derivative which has been identified as a designer drug.^[2][3]

DALT

Clinical data
Other names	N,N-Diallyltryptamine; DALT; DAT
Routes of administration	Oral, intramuscular injection[1]
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 Y
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 Y Key:LQEATNFJCMVKAC-UHFFFAOYSA-N Y
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Use and effects

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), the dose of DALT is greater than 40 mg orally and its duration is unknown.^[1] Its effects were not described.^[1] Per Stephen Szara and colleagues in much earlier publications 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][4][5]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

DALT activities

Target	Affinity (Ki, nM)
5-HT1A	100
5-HT1B	>10,000
5-HT1D	689
5-HT1E	378
5-HT1F	ND
5-HT2A	701
5-HT2B	61
5-HT2C	385
5-HT3	>10,000
5-HT4	ND
5-HT5A	>10,000
5-HT6	1,718
5-HT7	>10,000
α1A	1,663
α1B	1,369
α1D	>10,000
α2A	124
α2B	305
α2C	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 (Ki)
NETTooltip Norepinephrine transporter	1,121 (Ki)
DATTooltip Dopamine transporter	1,406 (Ki)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:[6][7][8][9]

The receptor interactions of DALT have been studied.^[6][7][8][9] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[10]

Chemistry

DALT has been used as an intermediate in the preparation of radiolabeled diethyltryptamine (DET).^[11]

Synthesis

The chemical synthesis of DALT has been described.^[1]

Analogues

Analogues of DALT include 4-HO-DALT, 4-AcO-DALT, 5-MeO-DALT, and methylallyltryptamine (MALT), among others.^[1]

History

DALT was first described in the scientific literature by Stephen Szara and colleagues by 1962.^[4][5]

See also

• Substituted tryptamine