NDTDI

Last updated
NDTDI
NDTDI structure.svg
NDTDI ball-and-stick structure.png
Clinical data
Other namesN-(2-Diethylcarbamoylethyl)-N-methyl-4,α-methylenetryptamine; N-(3-Diethylamino-3-oxopropyl)-N-methyl-4,α-methylenetryptamine; 9-Nor-LSD; 9-Desmethine-LSD; 8,10-Seco-LSD
Drug class Serotonergic psychedelic; Hallucinogen; Simplified/partial LSD analogue
ATC code
  • None
Legal status
Legal status
  • Illegal in Latvia
Identifiers
  • N,N-diethyl-3-(methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino)propanamide
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Formula C19H27N3O
Molar mass 313.445 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)CCN(C)C1Cc3cccc2ncc(C1)c23
  • InChI=1S/C19H27N3O/c1-4-22(5-2)18(23)9-10-21(3)16-11-14-7-6-8-17-19(14)15(12-16)13-20-17/h6-8,13,16,20H,4-5,9-12H2,1-3H3
  • Key:JECGWOMOCPQHDH-UHFFFAOYSA-N

NDTDI, also known as 9-desmethine-LSD, 9-nor-LSD, or 8,10-seco-LSD, is a psychedelic drug related to lysergic acid diethylamide (LSD). [1] [2] [3] [4] It is a tricyclic cyclized tryptamine and partial lysergamide and is a structurally simplified analogue of LSD. [2] The drug is specifically the analogue of LSD in which the carbon atom at position 9 of the ergoline ring system has been removed. [2] It has been reported to produce psychedelic effects similarly to LSD, but with much lower potency. [1] The pharmacology of NDTDI has not been studied. NDTDI was encountered as a novel designer drug by 2016. [1] [3] [4]

Contents

Structures of LSD (left), NDTDI (4-desmethine-LSD) (middle), and N-DEAOP-NMT (desvinyl-LSD) (right). LSD, 4-desmethine-LSD, and desvinyl-LSD.png
Structures of LSD (left), NDTDI (4-desmethine-LSD) (middle), and N-DEAOP-NMT (desvinyl-LSD) (right).

Interactions

Chemistry

Analogues

Analogues of NDTDI include RU-27849, RU-28306, RU-28251, Bay R 1531 (LY-197206), LY-293284, and LY-178210. Other partial/simplified lysergamides include DEIMDHPCA (4-nor-LSD), DEMPDHPCA (dides-B,C-LSD), and 10,11-seco-LSD, among others. Deletion of the carbon at positions 9 and 10 of the ergoline ring system result in a fully non-rigid tryptamine derivative, N-DEAOP-NMT (9,10-dinor-LSD). [5] [6]

History

NDTDI has been sold as a designer drug since 2016 and was first identified by a forensic laboratory in Slovenia in 2017. [3] NDTDI was made illegal in Latvia in March 2017. [4] [7]

Society and culture

Canada

NDTDI is not an explicitly nor implicitly controlled substance in Canada as of 2025. [8]

United States

NDTDI is not an explicitly controlled substance in the United States. [9] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. 1 2 3 "Latvian authorities apply temporary restriction on new psychoactive substance". Baltic News Network. 6 March 2017. Retrieved 30 January 2026.
  2. 1 2 3 "N,N-Diethyl-N3-methyl-N3-(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)-I(2)-alaninamide". PubChem. Retrieved 20 March 2025.
  3. 1 2 3 Analytical Report NDTDI (C19H27N3O) 3-({2-azatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),3,8(12),9-tetraen-6-yl}(methyl)amino)-N,N-diethylpropanamide (PDF), European Project Response
  4. 1 2 3 Autorizēties savā kontā (March 2017). "Par aizlieguma noteikšanu vielai NDTDI un tās saturošiem izstrādājumiem" [On the prohibition of the substance NDTDI and products containing it]. LIKUMI.LV (in Latvian). Retrieved 20 March 2025.
  5. ↑ Nichols DE (May 1973). Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Thesis). University of Iowa. p. 23. OCLC   1194694085. Sklar, et al. (53) found the diethylacrylamide adduct 20 to be approximately 1/10 as active as LSD in mice, although Norris and Blicke (54) reported 21 to have little oxytocic activity. [...] 20 = R = C2H5. 21 = R = CH3 [...]
  6. ↑ Norris PE, Blicke FF (December 1952). "Potential ergot substitutes: esters and amides of beta-amino acids". J Am Pharm Assoc. 41 (12): 637–639. doi:10.1002/jps.3030411204. PMID   13022416. Six esters and amides of derivatives of β-alanine which are related to lysergic acid have been prepared and tested for oxytocic activity. None of these products possess a significant oxytocic activity. [...] The purpose of this investigation was to synthesize amides and also esters of compounds (II–V) which represent fragments of the lysergic acid molecule in the hope that some of these products might possess oxytocic activity. Various modified fragments of the lysergic acid molecule have been synthesized previously; it was claimed that some of the compounds are active oxytocics (1—7). [...] Pharmacologic data indicated that none of the esters or amides of compounds II—V which were prepared possess a significant oxytocic action when compared to the clinically used oxytocics. However, the diethylamide of N-methyl-N-[β′-(3-indolyl)-ethyl]-β-alanine (IIIc) appeared to have an oxytocic activity approximately ten times stronger than that of the diethylamide of N-methyl-N-(β′-phenethyl)-β-alanine (IIc).
  7. ↑ "Par aizlieguma noteikšanu vielai NDTDI un tās…". www.vestnesis.lv (in Latvian). 6 March 2017. Retrieved 30 January 2026.
  8. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  9. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
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