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AL-LAD

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AL-LAD
Clinical data
Other namesALLAD; AllylLAD; Allyl-LAD; ALLYLAD; AllyLAD; ALLY-LAD; 6-Allyl-6-nor-LSD; 6-Allyl-6-nor-N,N-diethyllysergamide; 9,10-Didehydro-6-allyl-N,N-diethylergoline-8β-carboxamide
Routes of
administration		Oral[1]
Drug classNon-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • AU: Unscheduled
  • CA: Unscheduled.
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Unscheduled, could be illegal if is sold for human consumption under the Federal Analogue Act.
  • Illegal in Denmark, Sweden, Switzerland and France, could be illegal in many countries if is sold for human consumption or under the several analogue acts[2]
Pharmacokinetic data
Onset of action15–20 minutes or hours[1]
Duration of action6–8 hours[1]
Identifiers
  • (6aR,9R)-N,N-diethyl-7-prop-2-enyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H27N3O
Molar mass349.478 g·mol−1
3D model (JSmol)
  • [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@@H](C(=O)N(CC)CC)CN2CC=C)c34
  • InChI=1S/C22H27N3O/c1-4-10-25-14-16(22(26)24(5-2)6-3)11-18-17-8-7-9-19-21(17)15(13-23-19)12-20(18)25/h4,7-9,11,13,16,20,23H,1,5-6,10,12,14H2,2-3H3/t16-,20-/m1/s1 checkY
  • Key:JCQLEPDZFXGHHQ-OXQOHEQNSA-N checkY
  (verify)

AL-LAD, or ALLAD, also known as ALLY-LAD or as 6-allyl-6-nor-LSD, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).[3][4] It is taken orally.[1]

The drug interacts with serotonin and dopamine receptors and is known to act as an agonist of the serotonin 5-HT2A receptor similarly to LSD.[5][6][7][8] AL-LAD produces psychedelic-like effects in animals.[7][3][9][10] It is closely structurally related to LSD and to other psychedelic lysergamides such as ETH-LAD and PRO-LAD.[7]

AL-LAD was first described in the scientific literature by 1976.[11] Subsequently, it was described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines i Have Known And Loved).[1] AL-LAD was encountered as a novel designer recreational drug by 2015.[4][12] The related drugs 1P-AL-LAD, 1cP-AL-LAD, and 1T-AL-LAD are thought to function as prodrugs of AL-LAD and have also been encountered as designer drugs in the 2020s.[13][14][15][16][17]

Use and effects

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AL-LAD on blotter paper.

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin describes the dose range of AL-LAD as 80 to 160 μg and its duration as 6 to 8 hours.[1] In other publications however, Shulgin listed its dose range as 50 to 150 μg.[18][19] A typical or moderate dose may be around 100 μg.[9][18][19] The drug appears to be roughly equipotent with LSD, which has a listed dose range of 50 to 200 μg.[20][18][19][1][21] AL-LAD's duration appears to be shorter than that of LSD, which is said to have a duration of 8 to 12 hours.[1][21][22] The onset of AL-LAD has been reported to be within 15 to 20 minutes, but others reported a slower and more gradual onset building up over a few hours.[1] It has also been reported to have a very long "down-ramp" of effects.[1]

AL-LAD has been described as producing similar effects to LSD and as being "really trippy" similarly, but to lack the "vaguely sinister push" of LSD.[1] In addition, it has been reported to have less visual distortion than LSD.[1] The experience has been described as "simply beautiful".[1] Its effects have been reported to include waves of intensification, no closed-eye visuals to superb mental imagery, mild visual distortion, open-eye visuals including floors melting and patterns on walls and ceilings flowing, some time dilation, separation from surrounding world, loss of contact with body, body feeling "blob-like", feeling stoned, music and erotic enhancement, clear thinking and good interpretation, mental and physical excitation, mood fluctuations, emotional lability, crying, opening up of repressed feelings, and in one case social distance and avoidance.[1] Some individuals specifically reported no fear, panic, or body disturbance.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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AL-LAD has been found to interact with the serotonin 5-HT1 and 5-HT2 receptors and with the dopamine D1 and D2 receptors.[5][6][7][8] It is known to act as a potent full agonist of the serotonin 5-HT2A receptor.[8]

The drug was about 3.5-fold more potent than LSD in substituting for LSD in drug discrimination tests in rodents.[7][3][9] Conversely however, AL-LAD was similar in potency to LSD in humans.[20][1] AL-LAD produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[10][4][9] It was slightly less potent than LSD in producing the head-twitch response in rodents.[9]

Pharmacokinetics

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The in-vitro metabolism of AL-LAD has been studied.[23][13]

Chemistry

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AL-LAD, also known as 6-allyl-6-nor-LSD or as 6-allyl-6-nor-N,N-diethyllysergamide, is a synthetic substituted lysergamide and a 6-substituted derivative of nor-LSD (LAD).[1]

Detection

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AL-LAD does not cause a color change with the Marquis, Mecke or Mandelin reagents,[24] but does cause the Ehrlich's reagent to turn purple because of the presence of the indole moiety in its structure.

Synthesis

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The chemical synthesis of AL-LAD has been described.[1] It is starting from nor-LSD as a precursor, using allyl bromide as a reactant.[1]

Analogues

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AL-LAD is closely related to other 6-substituted lysergamides such as LSD (METH-LAD), ETH-LAD, PRO-LAD, and MAL-LAD, among others.[1] Ester prodrugs of AL-LAD include 1P-AL-LAD, 1cP-AL-LAD, and 1T-AL-LAD.[13][14][15][16][17]

History

[edit]

AL-LAD was first described in the scientific literature by Tetsukichi Niwaguchi and colleagues in 1976.[4][11] Subsequently, it was further studied by Andrew J. Hoffman and David E. Nichols in 1985.[25] Alexander Shulgin described the effects of AL-LAD in humans in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a novel designer drug in Europe by 2015.[4][12]

Society and culture

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International

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AL-LAD is not scheduled by the United Nations' Convention on Psychotropic Substances overcome is legal ever that doesn't be sold for recreational usage, could be sold for medical or research purposes like a research chemical..[26]

Denmark

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AL-LAD is illegal in Denmark.[27]

Finland

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Listed in a decree of the government's psychoactive substances banned from the consumer market.[28][29]

France

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AL-LAD is illegal in France.[30]

Latvia

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AL-LAD is possibly illegal in Latvia. Although it isn't specifically scheduled, it may be controlled as an LSD structural analogue due to an amendment made on June 1, 2015.[31]

Sweden

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The Riksdag added AL-LAD to Narcotic Drugs Punishments Act under Swedish schedule I ("substances, plant materials and fungi which normally do not have medical use" ) as of January 26, 2016, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:35 listed as 6-allyl-6-nor-LSD, AL-LAD, and 6-allyl-N,N-dietyl-9,10-didehydroergolin-8-karboxamid.[32]

Switzerland

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AL-LAD is illegal in Switzerland.[33]

United Kingdom

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AL-LAD is illegal in the UK. On June 10, 2014 the UK Advisory Council on the Misuse of Drugs (ACMD) recommended that AL-LAD be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying any harm associated with its use.[34] The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014.

United States

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AL-LAD is a Controlled Substance at the federal level in the United States,[35] AL-LAD could be legally considered an analogue of the Schedule I drug LSD, therefore, sales, possession or consumption for recreational not medical nor scientific use could be prosecuted under the Federal Analogue Act.[36]

See also

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References

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  1. ^ a b c d e f g h i j k l m n o p q r s t u "#1 AL-LAD". Isomer Design. Retrieved 5 April 2025.
  2. ^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" [Order of May 20, 2021 amending the order of February 22, 1990 setting the list of substances classified as narcotics]. Journal officiel de la République française [Official Journal of the French Republic (JORF)] (in French). 20 May 2021.
  3. ^ a b c Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. TABLE 1 Effects of N-(6)-Alkyl Subtituents on LSD-Like Behavior and Serotonin Receptor Affinity in Rats [...]
  4. ^ a b c d e Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, et al. (January 2017). "6 -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ)". Drug Testing and Analysis. 9 (1): 38–50. doi:10.1002/dta.1985. PMC 5411264. PMID 27265891.
  5. ^ a b Hoffman AJ (August 1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University.
  6. ^ a b Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB (April 1995). "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology. 118 (4): 401–409. doi:10.1007/BF02245940. PMID 7568626. S2CID 21484356.
  7. ^ a b c d e Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited". NIDA Research Monograph. 146: 52–73. PMID 8742794.
  8. ^ a b c McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 15 May 2025. Retrieved 27 May 2025 – via Purdue e-Pubs.{{cite thesis}}: CS1 maint: bot: original URL status unknown (link)
  9. ^ a b c d e Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Archived from the original (PDF) on 26 March 2025.
  10. ^ a b Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMC 5787039. PMID 28224459.
  11. ^ a b Niwaguchi T, Nakahara Y, Ishii H (1976). "Lysergic Acid Diethylamideおよび関連化合物に関する研究(第4報)Norlysergic Acidの各種Amide誘導体ならびに関連化合物の合成" [Studies on Lysergic Acid Diethylamide and Related Compounds. IV. Syntheses of Various Amide Derivatives of Norlysergic Acid and Related Compounds]. Yakugaku Zasshi. 96 (5): 673–678. doi:10.1248/yakushi1947.96.5_673. ISSN 0031-6903. PMID 987200. Retrieved 27 March 2025.
  12. ^ a b "2015 Annual Reports on the implementation of Council Decision 2005/387/JHA". Europol. 23 October 2018. Retrieved 5 April 2025.
  13. ^ a b c Brandt SD, Kavanagh PV, Westphal F, Pulver B, Schwelm HM, Whitelock K, Stratford A, Auwärter V, Halberstadt AL (August 2022). "Analytical profile, in vitro metabolism and behavioral properties of the lysergamide 1P-AL-LAD". Drug Test Anal. 14 (8): 1503–1518. doi:10.1002/dta.3281. PMC 9546273. PMID 35524430.
  14. ^ a b Kavanagh PV, Westphal F, Pulver B, Schwelm HM, Stratford A, Auwärter V, Chapman SJ, Halberstadt AL, Brandt SD (March 2023). "Analytical profile of the lysergamide 1cP-AL-LAD and detection of impurities". Drug Test Anal. 15 (3): 277–291. doi:10.1002/dta.3397. PMID 36321499.
  15. ^ a b Tanaka R, Kawamura M, Mizutani S, Kikura-Hanajiri R (July 2023). "Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products". Forensic Toxicol. 41 (2): 294–303. doi:10.1007/s11419-023-00661-1. PMC 10310582. PMID 36809464.
  16. ^ a b Tanaka R, Kawamura M, Ito M, Kikura-Hanajiri R (July 2025). "Identification of two lysergic acid diethylamide analogs, 1-(3-(trimethylsilyl) propionyl) lysergic acid diethylamide (1S-LSD) and 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD), in paper sheet products distributed on the internet". Forensic Toxicol. 43 (2): 370–376. doi:10.1007/s11419-025-00718-3. PMID 40180768.
  17. ^ a b Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Kanamori T, Iwata YT (April 2025). "Synthesis and analytical characterization of 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD)". Drug Test Anal. 17 (4): 494–501. doi:10.1002/dta.3747. PMID 38922764.
  18. ^ a b c Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023.
  19. ^ a b c Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
  20. ^ a b Nichols DE (April 2016). "Psychedelics". Pharmacol Rev. 68 (2): 264–355. doi:10.1124/pr.115.011478. PMC 4813425. PMID 26841800.
  21. ^ a b Alexander T. Shulgin, Ann Shulgin (1997). "#26. LSD-25 Acid; Lysergide; D-Lysergic Acid Diethylamide; Meth-LAD; D-Lysergamide, N,N-Diethyl; N,N-Diethyl-D-Lysergamide; 9,10-Didehydro-N,N-Diethyl-6-Methylergoline-8b-Carboxamide". TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. pp. 490–499. ISBN 978-0-9630096-9-2. OCLC 38503252.
  22. ^ Hassan Z, Bosch OG, Singh D, Narayanan S, Kasinather BV, Seifritz E, Kornhuber J, Quednow BB, Müller CP (2017). "Novel Psychoactive Substances-Recent Progress on Neuropharmacological Mechanisms of Action for Selected Drugs". Front Psychiatry. 8 152. doi:10.3389/fpsyt.2017.00152. PMC 5563308. PMID 28868040. Shulgin also described novel ergolines such as N-allyl-nor-lysergic acid diethylamide (AL-LAD), N-ethyl-nor-lysergic acid diethylamide (ETH-LAD), and N-propyl-nor-lysergic acid diethylamide (PRO-LAD) (200). These LSD-analogs are as potent as LSD (potency relative to LSD in human: AL-LAD: 110%, ETH-LAD: 140%, PRO-LAD: 90%), but AL-LAD and PRO-LAD have shorter duration of action (6–8 h) as ETH-LAD and LSD (both: 8–12 h) (189, 200).
  23. ^ Wagmann L, Richter LH, Kehl T, Wack F, Bergstrand MP, Brandt SD, Stratford A, Maurer HH, Meyer MR (July 2019). "In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures". Anal Bioanal Chem. 411 (19): 4751–4763. doi:10.1007/s00216-018-1558-9. PMID 30617391.
  24. ^ Ecstasydata. "AL-LAD (Not sold as ecstasy)". EcstasyData.org. Archived from the original on 2013-12-26. Retrieved 2013-12-25.
  25. ^ Hoffman AJ, Nichols DE (September 1985). "Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives". J Med Chem. 28 (9): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.
  26. ^ Rupprich S. "Conventions". www.unodc.org. Archived from the original on 12 January 2018. Retrieved 4 May 2018.
  27. ^ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015. Archived from the original on 2016-06-09.
  28. ^ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 166/2016" [FINLEX ® - Legislation in original form: Government Decree on the consumer market... 166/2016]. www.finlex.fi. Retrieved June 11, 2023.
  29. ^ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 225/2017". www.finlex.fi (in Finnish). Retrieved June 11, 2023.
  30. ^ "Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". Republique Française. May 2021.
  31. ^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations on controlled narcotic substances, psychotropic substances and precursors in Latvia]. LIKUMI.LV. Archived from the original on 4 May 2018. Retrieved 4 May 2018.
  32. ^ "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m." [Joint constitutional collection on health care, social services, pharmaceuticals, public health, etc.] (PDF). Lakemedelsverket (in Swedish). Archived (PDF) from the original on 2017-10-31. Retrieved 2017-04-21.
  33. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" [EDI ordinance on the lists of narcotics, psychotropic substances, precursor substances and auxiliary chemicals] (in German). Der Bundesrat. Archived from the original on 2016-01-23.
  34. ^ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Archived (PDF) from the original on 6 October 2014. Retrieved 10 June 2014.
  35. ^ "PART 1308 - Section 1308.11 Schedule I". www.deadiversion.usdoj.gov. Archived from the original on 27 August 2009. Retrieved 4 May 2018.
  36. ^ "Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary". www.erowid.org. Archived from the original on 17 April 2018. Retrieved 4 May 2018.
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