Chemistry:AL-LAD

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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).[1][2] It is taken orally.[3]

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.[4][5][6][7] AL-LAD produces psychedelic-like effects in animals.[6][1][8][9] It is closely structurally related to LSD and to other psychedelic lysergamides such as ETH-LAD and PRO-LAD.[6]

AL-LAD was first described in the scientific literature by 1976.[10] Subsequently, it was described by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines i Have Known And Loved).[3] AL-LAD was encountered as a novel designer recreational drug by 2015.[2][11] 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.[12][13][14][15][16]

Use and effects

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.[3] In other publications however, Shulgin listed its dose range as 50 to 150 μg.[17][18] A typical or moderate dose may be around 100 μg.[8][17][18] The drug appears to be roughly equipotent with LSD, which has a listed dose range of 50 to 200 μg.[19][17][18][3][20] AL-LAD's duration appears to be shorter than that of LSD, which is said to have a duration of 8 to 12 hours.[3][20][21] 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.[3] It has also been reported to have a very long "down-ramp" of effects.[3]

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.[3] In addition, it has been reported to have less visual distortion than LSD.[3] The experience has been described as "simply beautiful".[3] 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.[3] Some individuals specifically reported no fear, panic, or body disturbance.[3]

Interactions

Pharmacology

Pharmacodynamics

AL-LAD has been found to interact with the serotonin 5-HT1 and 5-HT2 receptors and with the dopamine D1 and D2 receptors.[4][5][6][7] It is known to act as a potent full agonist of the serotonin 5-HT2A receptor.[7]

The drug was about 3.5-fold more potent than LSD in substituting for LSD in drug discrimination tests in rodents.[6][1][8] Conversely however, AL-LAD was similar in potency to LSD in humans.[19][3] AL-LAD produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[9][2][8] It was slightly less potent than LSD in producing the head-twitch response in rodents.[8]

Pharmacokinetics

The in-vitro metabolism of AL-LAD has been studied.[22][12]

Chemistry

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).[3]

Detection

AL-LAD does not cause a color change with the Marquis, Mecke or Mandelin reagents,[23] but does cause the Ehrlich's reagent to turn purple because of the presence of the indole moiety in its structure.

Synthesis

The chemical synthesis of AL-LAD has been described.[3] It is starting from nor-LSD as a precursor, using allyl bromide as a reactant.[3]

Analogues

AL-LAD is closely related to other 6-substituted lysergamides such as LSD (METH-LAD), ETH-LAD, PRO-LAD, and MAL-LAD, among others.[3] Ester prodrugs of AL-LAD include 1P-AL-LAD, 1cP-AL-LAD, and 1T-AL-LAD.[12][13][14][15][16]

History

AL-LAD was first described in the scientific literature by Tetsukichi Niwaguchi and colleagues in 1976.[2][10] Subsequently, it was further studied by Andrew J. Hoffman and David E. Nichols in 1985.[24] Alexander Shulgin described the effects of AL-LAD in humans in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[3] The drug was encountered as a novel designer drug in Europe by 2015.[2][11]

Society and culture

International

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..[25]

Denmark

AL-LAD is illegal in Denmark.[26]

Finland

Listed in a decree of the government's psychoactive substances banned from the consumer market.[27][28]

France

AL-LAD is illegal in France.[29]

Latvia

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.[30]

Sweden

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.[31]

Switzerland

AL-LAD is illegal in Switzerland.[32]

United Kingdom

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.[33] 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

AL-LAD is a Controlled Substance at the federal level in the United States,[34] 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.[35]

See also

References

  1. ↑ 1.0 1.1 1.2 "Stereochemical Aspects of Hallucinogenesis". Biochemistry and Physiology of Substance Abuse. 3. Boca Raton, Fla.: CRC Press. 1991. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. https://bitnest.netfirms.com/external/Books/BiochemistryPhysiologySubstanceAbuse3.1. "TABLE 1 Effects of N-(6)-Alkyl Subtituents on LSD-Like Behavior and Serotonin Receptor Affinity in Rats [...]" 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "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. January 2017. doi:10.1002/dta.1985. PMID 27265891. 
  3. ↑ 3.00 3.01 3.02 3.03 3.04 3.05 3.06 3.07 3.08 3.09 3.10 3.11 3.12 3.13 3.14 3.15 3.16 3.17 Cite error: Invalid <ref> tag; no text was provided for refs named TiHKAL
  4. ↑ 4.0 4.1 Hoffman AJ (August 1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University.
  5. ↑ 5.0 5.1 "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology 118 (4): 401–409. April 1995. doi:10.1007/BF02245940. PMID 7568626. 
  6. ↑ 6.0 6.1 6.2 6.3 6.4 "Lysergamides revisited". NIDA Research Monograph 146: 52–73. 1994. PMID 8742794. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=dbc3139042e2b2baf5a2e6c65edc6afe9b131f79. 
  7. ↑ 7.0 7.1 7.2 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)
  8. ↑ 8.0 8.1 8.2 8.3 8.4 "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. https://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf. 
  9. ↑ 9.0 9.1 "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Current Topics in Behavioral Neurosciences. 36. 2018. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. 
  10. ↑ 10.0 10.1 "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". Yakugaku Zasshi 96 (5): 673–678. 1976. doi:10.1248/yakushi1947.96.5_673. ISSN 0031-6903. PMID 987200. https://www.jstage.jst.go.jp/article/yakushi1947/96/5/96_5_673/_pdf. Retrieved 27 March 2025. 
  11. ↑ 11.0 11.1 "2015 Annual Reports on the implementation of Council Decision 2005/387/JHA". 23 October 2018. https://www.europol.europa.eu/publications-events/publications/emcdda%E2%80%93europol-2005-2015-annual-reports-implementation-of-council-decision-2005/387/jha. 
  12. ↑ 12.0 12.1 12.2 "Analytical profile, in vitro metabolism and behavioral properties of the lysergamide 1P-AL-LAD". Drug Test Anal 14 (8): 1503–1518. August 2022. doi:10.1002/dta.3281. PMID 35524430. 
  13. ↑ 13.0 13.1 "Analytical profile of the lysergamide 1cP-AL-LAD and detection of impurities". Drug Test Anal 15 (3): 277–291. March 2023. doi:10.1002/dta.3397. PMID 36321499. 
  14. ↑ 14.0 14.1 "Identification of LSD analogs, 1cP-AL-LAD, 1cP-MIPLA, 1V-LSD and LSZ in sheet products". Forensic Toxicol 41 (2): 294–303. July 2023. doi:10.1007/s11419-023-00661-1. PMID 36809464. 
  15. ↑ 15.0 15.1 "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. July 2025. doi:10.1007/s11419-025-00718-3. PMID 40180768. 
  16. ↑ 16.0 16.1 "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. April 2025. doi:10.1002/dta.3747. PMID 38922764. 
  17. ↑ 17.0 17.1 17.2 "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr 146: 74–91. 1994. PMID 8742795. https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79. 
  18. ↑ 18.0 18.1 18.2 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6. Retrieved 1 February 2025. 
  19. ↑ 19.0 19.1 "Psychedelics". Pharmacol Rev 68 (2): 264–355. April 2016. doi:10.1124/pr.115.011478. PMID 26841800. 
  20. ↑ 20.0 20.1 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. https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml. 
  21. ↑ "Novel Psychoactive Substances-Recent Progress on Neuropharmacological Mechanisms of Action for Selected Drugs". Front Psychiatry 8. 2017. doi:10.3389/fpsyt.2017.00152. 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).". 
  22. ↑ "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. July 2019. doi:10.1007/s00216-018-1558-9. PMID 30617391. 
  23. ↑ Ecstasydata. "AL-LAD (Not sold as ecstasy)". EcstasyData.org. http://www.ecstasydata.org/view.php?id=2829. 
  24. ↑ "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. September 1985. doi:10.1021/jm00147a022. PMID 4032428. 
  25. ↑ "Conventions". https://www.unodc.org/unodc/en/commissions/CND/conventions.html. 
  26. ↑ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015. http://laegemiddelstyrelsen.dk/en/licensing/company-authorisations-and-registrations/euphoriant-substances/lists-of-substances. 
  27. ↑ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 166/2016". https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2016/166. 
  28. ↑ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 225/2017" (in fi). https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2017/225. 
  29. ↑ "Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". Republique Française. May 2021. https://www.legifrance.gouv.fr/loda/id/JORFTEXT000000533085/2020-11-20/. 
  30. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem". http://likumi.lv/doc.php?id=121086. 
  31. ↑ "Gemensamma författningssamlingen avseende hälso- och sjukvård, socialtjänst, läkemedel, folkhälsa m.m." (in sv). Lakemedelsverket. https://lakemedelsverket.se/upload/lvfs/HSLF-FS/HSLFS-FS_2015_35.pdf. 
  32. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in de). Der Bundesrat. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 
  33. ↑ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines". UK Home Office. p. 12. https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf. 
  34. ↑ "PART 1308 - Section 1308.11 Schedule I". http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm. 
  35. ↑ "Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary". https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml. 

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