AL-LAD

Last updated
AL-LAD
AL-LAD structure.svg
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 and France, could be illegal in many countries if is sold for human consumption or under the several analogue acts [1] Sweden and Switzerland
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
Formula C22H27N3O
Molar mass 349.478 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 Yes check.svgY
  • Key:JCQLEPDZFXGHHQ-OXQOHEQNSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD). [2] It is described by Alexander Shulgin in the book TiHKAL (Tryptamines i Have Known And Loved). It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant.

Contents

Effects in humans

AL-LAD on blotter paper AL-LAD blotter.jpg
AL-LAD on blotter paper

While AL-LAD has subtly different effects than LSD, and appears to be slightly shorter lasting, their potencies are similar; [3] [4] an active dose of AL-LAD is reported to be between 50 and 150 micrograms. [5] AL-LAD has a known but short and highly uncommon history of recreational human use, which originated in Ireland and the UK, but spread internationally.[ citation needed ]

Chemistry

AL-LAD does not cause a color change with the Marquis, Mecke or Mandelin reagents, [6] but does cause the Ehrlich's reagent to turn purple because of the presence of the indole moiety in its structure.

AL-LAD is not scheduled by the United Nations' Convention on Psychotropic Substances. [7]

Denmark

AL-LAD is illegal in Denmark. [8]

France

AL-LAD is illegal in France. [9]

Finland

Listed in a decree of the government's psychoactive substances banned from the consumer market. [10] [11]

Latvia

AL-LAD is possibly illegal in Latvia. Although it isn't specifically scheduled, it may be controlled as an LSD structural analog due to an amendment made on June 1, 2015. [12]

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. [13]

Switzerland

AL-LAD is illegal in Switzerland. [14]

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. [15] 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, [16] AL-LAD is legally considered an analog of LSD, therefore, sales or possession with intent for human consumption could be prosecuted under the Federal Analogue Act. [17]

See also

Related Research Articles

<span class="mw-page-title-main">Ergine</span> Chemical compound

Ergine, also known as d-lysergic acid amide (LSA) and d-lysergamide, is an ergoline alkaloid that occurs in various species of vines of the Convolvulaceae and some species of fungi. The psychedelic properties in the seeds of ololiuhqui, Hawaiian baby woodrose and morning glories have been linked to ergine and/or isoergine, its epimer, as it is an alkaloid present in the seeds.

<span class="mw-page-title-main">Lysergic acid</span> Precursor for a range of ergoline alkaloids produced by the ergot fungus

Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Turbina corymbosa (ololiuhqui), Argyreia nervosa, and Ipomoea tricolor.

<span class="mw-page-title-main">2C-D</span> Chemical compound

2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg. Lower doses of 10 mg or less have been explored for microdosing.

<span class="mw-page-title-main">2,5-Dimethoxy-4-methylamphetamine</span> Chemical compound

2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">Trifluoromethylphenylpiperazine</span> Chemical compound

3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the phenylpiperazine chemical class and is a substituted piperazine. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy").

<span class="mw-page-title-main">5-MeO-MiPT</span> Chemical compound

5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

<span class="mw-page-title-main">Lysergamides</span> Class of chemical compounds

Amides of lysergic acid are collectively known as lysergamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine receptors. Lysergamides contain an embedded tryptamine structure, and as a result can produce similar, often psychedelic, effects to those of the true tryptamines.

<span class="mw-page-title-main">ALD-52</span> Chemical compound

ALD-52, also known as 1-acetyl-LSD, has chemical structural features similar to lysergic acid diethylamide (LSD), a known psychedelic drug. Similarly, ALD-52 has been reported to produce psychoactive effects, but its pharmacological effects on humans are poorly understood. Given its psychoactive properties, it has been reported to be consumed as a recreational drug, and the purported first confirmed detection of the substance on the illicit market occurred in April 2016.

<span class="mw-page-title-main">ETH-LAD</span> Chemical compound

ETH-LAD, 6-ethyl-6-nor-lysergic acid diethylamide is an analogue of LSD. Its human psychopharmacology was first described by Alexander Shulgin in the book TiHKAL. ETH-LAD is a psychedelic drug similar to LSD, and is slightly more potent than LSD itself, with an active dose reported at between 20 and 150 micrograms. ETH-LAD has subtly different effects to LSD, described as less demanding. The true tryptamine counterpart of ETH-LAD is MET, a simplified version of this structure.

<span class="mw-page-title-main">PRO-LAD</span> Chemical compound

PRO-LAD is an analogue of LSD. It is described by Alexander Shulgin in the book TiHKAL. PRO-LAD is a psychedelic drug similar to LSD, and is around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.

<span class="mw-page-title-main">BU-LAD</span> Chemical compound

BU-LAD, also known as 6-butyl-6-nor-lysergic acid diethylamide, is an analogue of LSD first made by Alexander Shulgin and reported in the book TiHKAL. BU-LAD is a psychedelic drug similar to LSD, but is significantly less potent than LSD, with a dose of 500 micrograms producing only mild effects.

<span class="mw-page-title-main">LSM-775</span> Chemical compound

N-Morpholinyllysergamide (LSM-775) is a derivative of ergine. It is less potent than LSD but is reported to have some LSD-like effects at doses ranging from 75 to 700 micrograms and a shorter duration. There are fewer signs of cardiovascular stimulation and peripheral toxicity with LSM-775 compared to LSD.

<span class="mw-page-title-main">Lysergic acid 2,4-dimethylazetidide</span> Chemical compound

Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.

<span class="mw-page-title-main">6-Isopropyl-6-nor-lysergic acid diethylamide</span> Chemical compound

6-Isopropyl-6-nor-lysergic acid diethylamide (IP-LAD) is an analog of lysergic acid diethylamide (LSD) developed by the team of David E. Nichols. In studies on mice, it was found to be approximately 40% the potency of LSD, compared to the 60% increase in potency seen with ETH-LAD, 2-fold potency increase of AL-LAD, and roughly equivalent potency of PRO-LAD.

<span class="mw-page-title-main">1P-LSD</span> Chemical compound

1P-LSD is a psychedelic drug of the lysergamide class that is a derivative and functional analogue of LSD and a homologue of ALD-52. It originated in 2015 when it appeared a designer drug sold online. It modifies the LSD molecule by adding a propionyl group to the nitrogen molecule of LSD's indole group.

<span class="mw-page-title-main">1P-ETH-LAD</span> Chemical compound

1P-ETH-LAD is an analog of LSD. 1P-ETH-LAD is a psychedelic drug similar to LSD. Research has shown formation of ETH-LAD from 1P-ETH-LAD incubated in human serum, suggesting that it functions as a prodrug. It is part of the lysergamide chemical class. Like ETH-LAD, this drug has been reported to be significantly more potent than LSD itself, and is reported to largely mimic ETH-LAD's psychedelic effects.

<span class="mw-page-title-main">1cP-LSD</span> Chemical compound

1cP-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. In tests on mice it was found to be an active psychedelic with similar potency to 1P-LSD.

<span class="mw-page-title-main">1B-LSD</span> Chemical compound

1B-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. In tests on mice it was found to be an active psychedelic, though with only around 1/7 the potency of LSD itself.

<span class="mw-page-title-main">1V-LSD</span> Chemical compound

1V-LSD, sometimes nicknamed Valerie, is a psychotropic substance and a research chemical with psychedelic effects. 1V-LSD is an artificial derivative of natural lysergic acid, which occurs in ergot alkaloids, as well as being an analogue of LSD. 1V-LSD has been sold online until an amendment to the German NpSG was enforced in 2022 which controls 1P-LSD and now 1cP-LSD, 1V-LSD and several other lysergamides.

References

  1. ↑ "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.
  2. ↑ 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.
  3. ↑ Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. Vol. 32. Springer International Publishing. pp. 351–380. doi:10.1007/7854_2016_15. ISBN   978-3-319-52442-9. OCLC   643052237. PMID   27272067.
  4. ↑ 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): 1252–5. doi:10.1021/jm00147a022. PMID   4032428.
  5. ↑ Shulgin A (1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 392. ISBN   978-0-9630096-9-2. Archived from the original on 2015-11-18.
  6. ↑ Ecstasydata. "AL-LAD (Not sold as ecstasy)". EcstasyData.org. Archived from the original on 2013-12-26. Retrieved 2013-12-25.
  7. ↑ Rupprich S. "Conventions". www.unodc.org. Archived from the original on 12 January 2018. Retrieved 4 May 2018.
  8. ↑ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015. Archived from the original on 2016-06-09.
  9. ↑ "Arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". Republique Française. May 2021.
  10. ↑ "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.
  11. ↑ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 225/2017". www.finlex.fi (in Finnish). Retrieved June 11, 2023.
  12. ↑ "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.
  13. ↑ "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.
  14. ↑ "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.
  15. ↑ 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.
  16. ↑ "PART 1308 - Section 1308.11 Schedule I". www.deadiversion.usdoj.gov. Archived from the original on 27 August 2009. Retrieved 4 May 2018.
  17. ↑ "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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