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Details

Stereochemistry ACHIRAL
Molecular Formula C17H22N2O
Molecular Weight 270.3694
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N,N-DIALLYL-5-METHOXYTRYPTAMINE

SMILES

COC1=CC2=C(NC=C2CCN(CC=C)CC=C)C=C1

InChI

InChIKey=HGRHWEAUHXYNNP-UHFFFAOYSA-N
InChI=1S/C17H22N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h4-7,12-13,18H,1-2,8-11H2,3H3

HIDE SMILES / InChI

Molecular Formula C17H22N2O
Molecular Weight 270.3694
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

N,N-Diallyl-5-methoxytryptamine (N-Allyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl] prop-2-en-1- amine, 5-MeO-DALT) is a psychedelic tryptamine first synthesized by Alexander Shulgin. N,N-Diallyl-5-methoxytryptamine is used as a hallucinogenic drug has been reported only occasionally in online user fora. It is controlled in only a few countries worldwide. There is little scientifically-based literature on the pharmacological, physiological, psychopharmacological, toxicological and epidemiological characteristics of 5-MeO-DALT. Most of the information published on the effects of 5-MeO-DALT is derived from first-hand personal accounts presented in discussion fora. User reports suggest that its effects are felt within 15 min of being taken orally, and its full effects within 30 min. User reports on 5-MeO-DALT state rapid, strong entheogenic effect, euphoric, sensual, energised bodies, visual hallucinations (similar to those experienced with MDMA), loss of control of limbs making walking difficult, and ‘out of body’ type experience Acute mental effects reported include: increased alertness and awareness, increased arousal, and agitation.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
27.54 nM [EC50]
9.4 nM [EC50]
5.5 nM [EC50]
501.2 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Recommended oral doses from 12 to 25 mg for normal use, although initial doses of up to 50mg have been reported
Route of Administration: Other
In Vitro Use Guide
[35S]GTPgamma S Binding Assay were used for activity evaluation. The assay buffer consisted of 25mM HEPES, pH 7.6, 7mM MgCl2, 100mM NaCl, 1mM EDTA, 0.2mM DTT and 10mkM DPCPX. To each well was added various concentrations of drugs, DA, 5-HT, NE or assay buffer and the mixture of thawed the brain-membranes (2mkg protein/well for the striatum and 4m g protein/well for the cortex) and 150mkM GDP. This mixture was pre-incubated at 30 °C for 20 min in a shaking incubator. Incubation was started by adding 0.1 nM [35S]GTPg S to a total volume of 100mkl, and continued at 30 °C for 90 min in a shaking incubator. The reaction was stopped by rapid filtration over a GF/C glass fiber filter using a cell harvester (FilterMate, PerkinElmer, MA, U.S.A.). The pellets retained on the filter were washed with ice-cold 20mM HEPES buffer (pH 7.6, 5mM MgCl2, 100mM NaCl). Retained membrane-bound radioactivity on the filter was measured by liquid scintillation counting.
Substance Class Chemical
Record UNII
V25VK0QTAA
Record Status Validated (UNII)
Record Version