Jump to content

PRO-LAD

From Wikipedia, the free encyclopedia
(Redirected from 6-Propyl-nor-LSD)
PRO-LAD
Clinical data
Other namesPROLAD; 6-Propyl-6-nor-LSD; 6-Propyl-nor-LSD; 6-Propyl-6-norlysergic acid diethylamide; N,N-Diethyl-6-propyl-9,10-didehydroergoline-8β-carboxamide
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Onset of action≤15 minutes[1]
Duration of action6–8 hours[1]
Identifiers
  • (6aR,9R)-N,N-diethyl-7-propyl-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
FormulaC22H29N3O
Molar mass351.494 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@@H]2C=C1c3cccc4[nH]cc(C[C@H]1N(C2)CCC)c34
  • InChI=1S/C22H29N3O/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/h7-9,11,13,16,20,23H,4-6,10,12,14H2,1-3H3/t16-,20-/m1/s1 checkY
  • Key:HZKYLVLOBYNKKM-OXQOHEQNSA-N checkY
  (verify)

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

Use and effects

[edit]

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) and other publications, PRO-LAD has a dose range of 100 to 200 μg or 80 to 175 μg orally and a duration of 6 to 8 hours.[1][4][5][6] The onset is within 15 minutes.[1] It has around the same potency as LSD, which has a listed dose range of 50 to 200 μg.[1][4][5] On the other hand, PRO-LAD has a shorter duration than LSD, which has a listed duration of 8 to 12 hours.[1][7]

The effects of PRO-LAD have been reported to include a lack of visuals and other psychedelic effects at lower doses, considerable visuals at higher doses, fantasy, synesthesia, clear thinking, lack of "cosmic-type" thinking, humor, pleasantness, dulled emotions, uncomfortableness, paranoia, and lightheadedness.[1] It has been described as having relatively light or moderate effects.[1] In addition, it is said to "not have any of the flavor of LSD", to be less visual than LSD, and to be "not up to LSD", if that is one's standard, as it is "basically not like LSD".[1][8]

Interactions

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

Pharmacology

[edit]

Pharmacodynamics

[edit]

PRO-LAD shows affinity for serotonin receptors, including for the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors.[9][10][11][6] It acts as a partial agonist of the serotonin 5-HT2A receptor similarly to LSD.[10]

The drug fully substitutes for LSD in rodent drug discrimination tests and with about the same or slightly greater potency than LSD itself.[9][6][3][11][12] On the other hand, it was about 2- to 3-fold less potent than ETH-LAD or AL-LAD.[9][6][3][11][12]

Chemistry

[edit]

Synthesis

[edit]

The chemical synthesis of PRO-LAD has been described.[1]

Analogues

[edit]

Analogues of PRO-LAD include LSD, ETH-LAD, IP-LAD, AL-LAD, BU-LAD, MAL-LAD, PARGY-LAD, CYP-LAD, FLUORETH-LAD, and FP-LAD, among others.[1][4][5][9]

History

[edit]

PRO-LAD was first described in the scientific literature by Tetsukichi Niwaguchi and colleagues in 1976.[13] Subsequently, it was studied and described by Andrew J. Hoffman and David E. Nichols in 1985.[12] The hallucinogenic effects of PRO-LAD in humans were first described by Nichols in a literature review via personal communication with Alexander Shulgin in 1986.[8] The drug was later described in greater detail by Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] PRO-LAD is said to have been encountered as a novel designer drug by 2015.[14][15]

Society and culture

[edit]
[edit]

Switzerland

[edit]

PRO-LAD is illegal in Switzerland as of December 2015.[16]

United Kingdom

[edit]

On June 10, 2014, the United Kingdom Advisory Council on the Misuse of Drugs (ACMD) recommended that PRO-LAD be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying it as ever having been sold or any harm associated with its use.[17] 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.

See also

[edit]

References

[edit]
  1. ^ a b c d e f g h i j k l m n o Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. https://www.erowid.org/library/books_online/tihkal/tihkal51.shtml
  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]. www.legifrance.gouv.fr (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 Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr. 146: 74–91. PMID 8742795.
  5. ^ 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.
  6. ^ a b c d Nichols DE (April 2016). "Psychedelics". Pharmacol Rev. 68 (2): 264–355. doi:10.1124/pr.115.011478. PMC 4813425. PMID 26841800.
  7. ^ 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).
  8. ^ a b Nichols DE (February 1986). "Studies of the relationship between molecular structure and hallucinogenic activity". Pharmacol Biochem Behav. 24 (2): 335–340. doi:10.1016/0091-3057(86)90362-x. PMID 3952123.
  9. ^ a b c d Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited". NIDA Research Monograph. 146: 52–73. PMID 8742794.
  10. ^ a b 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 25 March 2025 – via Purdue e-Pubs.
  11. ^ a b c Hoffman AJ (August 1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University. Table 7. 5-HT2 binding affinity of N(6)-alkyl norLSD derivatives. [...]
  12. ^ a b c 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". Journal of Medicinal Chemistry. 28 (9): 1252–1255. doi:10.1021/jm00147a022. PMID 4032428.
  13. ^ 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.
  14. ^ Schifano F, Papanti GD, Orsolini L, Corkery JM (July 2016). "Novel psychoactive substances: the pharmacology of stimulants and hallucinogens". Expert Rev Clin Pharmacol. 9 (7): 943–954. doi:10.1586/17512433.2016.1167597. hdl:2299/18468. PMID 26985969.
  15. ^ Wachełko O, Nowak K, Tusiewicz K, Zawadzki M, Szpot P (January 2025). "A highly sensitive UHPLC-MS/MS method for determining 15 designer LSD analogs in biological samples with application to stability studies". Analyst. 150 (2): 290–308. Bibcode:2025Ana...150..290W. doi:10.1039/d4an01361a. PMID 39636448.
  16. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" [Ordinance of the EDI on the lists of narcotics, psychotropic substances, precursor substances and auxiliary chemicals]. Der Bundesrat [The Federal Council] (in German).
  17. ^ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=PRO-LAD&oldid=1321061100"