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Description

AL-LAD Also known as:

  • (8β)-6-Allyl-N,N-diethyl-9,10-didehydroergolin-8-carboxamid[German][ACD/IUPAC Name]
  • (8β)-6-Allyl-N,N-diethyl-9,10-didehydroergoline-8-carboxamide[ACD/IUPAC Name]
  • (8β)-6-Allyl-N,N-diéthyl-9,10-didéhydroergoline-8-carboxamide[French][ACD/IUPAC Name]
  • (8β)-N,N-diethyl-6-(prop-2-en-1-yl)-9,10-didehydroergoline-8-carboxamide
  • Ergoline-8-carboxamide, 9,10-didehydro-N,N-diethyl-6-(2-propen-1-yl)-, (8β)-[ACD/Index Name]
  • N-ALLYLNORLYSERGIC ACID N,N-DIETHYLAMIDE
  • (6aR,9R)-7-allyl-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indol[4,3-fg]quinoline-9-carboxyamine[ACD/IUPAC Name]
  • (6aR,9R)-N,N-diethyl-7-prop-2-enyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
  • 7-Allyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid diethylamide
  • 8??-6-allyl-6-norlysergic acid diethylamide
  • AL-LAD

AL-LAD is a hallucinogenic drug, lysergamide and an analogue of LSD. It is reported as having some subtle experiential differences to LSD (such as increased visuals), and also appears to be slightly shorter lasting. AL-LAD doses are similar to those of LSD, depending on purity. Its availability on the Internet since 2013 has lead to strong popularity among the drug community.

Summary

AL-LAD is chemically similar to LSD and has a similar mechanism of action, working primarily by binding to serotonin receptors in the brain. AL-LAD was first investigated in 1984 by Andrew J. Hoffman and David Nichols as part of a series of LSD analogs, which also included ETH-LAD and PRO-LAD.

Its activity in humans was later documented by Alexander Shulgin in his book TiHKAL (“Tryptamines I Have Known and Loved”), in which it is described as “considerably less dramatic”. In 2013, AL-LAD appeared for sale on the research chemical market, where it has been commonly marketed alongside lysergamides such as 1P-LSD, ALD-52 and ETH-LAD as a legal, grey-market alternative to LSD. User reports describe the effects of AL-LAD as similar to those of LSD with some subtle differences.

It is thought to either be equally or moderately less potent than LSD itself, with an active dose reported at between 75 and 150 micrograms. It is often described as being more visually-oriented but with a less introspective headspace. It also has a moderately shorter duration and is generally considered to be a less anxiety-provoking and challenging version of LSD.

Very little data exists about the pharmacological properties, metabolism, and toxicity of AL-LAD. While it is often characterized by users as being generally more recreational and non-threatening compared to LSD, it is highly advised to approach this highly potent hallucinogenic substance with the proper amount of precaution and harm reduction practices if using it.

Chemistry

AL-LAD

AL-LAD

AL-LAD is a structural analog of lysergic acid, with an N,N-diethylamide functional group bound to RN of the chemical structure.

AL-LAD’s chemical structure contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (nor-lysergic acid).

Unlike LSD, AL-LAD does not contain a methyl group substituted at R6 of its nor-lysergic acid skeleton, this is represented by the nor- prefix.

Instead, AL-LAD is substituted at R6 with an allyl group comprised of a methylene bridge bound to a vinyl substituent.

At carbon 8 of the quinoline a N,N-diethyl carboxamide is bound. AL-LAD is a chiral compound with two stereocenters at R5 and R8.

AL-LAD, also called (+)-D-AL-LAD, has an absolute configuration of (5R, 8R).

The three other stereoisomers of AL-LAD do not have psychoactive properties.

Common NameN-ALLYLNORLYSERGIC ACID N,N-DIETHYLAMIDE
Systematic nameN-ALLYLNORLYSERGIC ACID N,N-DIETHYLAMIDE
FormulaC_{22}H_{27}N_{3}O
SMILESCCN(CC)C(=O)[[email protected]]1CN([[email protected]@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)CC=C
Std. InChiInChI=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
Std. InChiKeyJCQLEPDZFXGHHQ-OXQOHEQNSA-N
Avg. Mass349.4693 Da
Molecular Weight349.4693
Monoisotopic Mass349.215424 Da
Nominal Mass349
ChemSpider ID21106248

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Dose Chart

Oral
Light40-75ug
Common75-175ug
Strong175-250ug
Heavy250ug+

Duration Chart

AL-LAD Duration Data
Onset45-120 minutes
Duration4-6 hours
After-effects1-24 hours

Legal Status

AL-LAD is currently a gray area compound within many parts of the world. This means that it is not known to be specifically illegal within most countries, but people may still be charged for its possession under certain circumstances such as under analog laws and with the intent to sell or consume.

  • Austria: AL-LAD is technically not illegal but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD.
  • Denmark: As of August 25, 2015, AL-LAD is specifically named on the list of illegal substances.
  • Germany: AL-LAD is controlled under the NpSG (New Psychoactive Substances Act) as of July 18, 2019. Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.
  • Latvia: AL-LAD is illegal in Latvia. Although it isn't officially scheduled, it is controlled as an LSD structural analog due to an amendment made on June 1, 2015.
  • Sweden: Following its sale as a designer drug, AL-LAD was made illegal in Sweden on January 26, 2016.
  • Switzerland: 21 substances, including AL-LAD, were added to the list of illegal substances including on December 1, 2015.
  • Turkey: AL-LAD is illegal in Turkey as of February 2016.
  • United Kingdom: As of January 7, 2015, AL-LAD is specifically named in the U.K. Misuse of Drugs Act as a Class A controlled substance.
  • United States: AL-LAD is unscheduled but can be considered to be an analogue of LSD, which would make it illegal to possess for human consumption under the Federal Analogue Act.
  • Sources

    References

    1. Hoffman, Andrew J.; Nichols, David E. (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. :10.1021/jm00147a022.  0022-2623.
    2. Shulgin, Alexander; Shulgin, Ann (1997). "#1. AL-LAD". TiHKAL: The Continuation. United States: Transform Press.  0-9630096-9-9. OCLC 38503252.
    3. Brandt, S. D.; Kavanagh, P. V.; Westphal, F.; Elliott, S. P.; Wallach, J.; Colestock, T.; Burrow, T. E.; Chapman, S. J.; Stratford, A.; Nichols, D. E.; Halberstadt, A. L. (2016). "Return of the lysergamides. Part II: Analytical and behavioural characterization of N6‐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. :10.1002/dta.1985.  1942-7603.
    4. Armstrong, B. D.; Paik, E.; Chhith, S.; Lelievre, V.; Waschek, J. A.; Howard, S. G. (2004). "Potentiation of (DL)‐3,4‐methylenedioxymethamphetamine (MDMA)‐induced toxicity by the serotonin 2A receptior partial agonist d‐lysergic acid diethylamide (LSD), and the protection of same by the serotonin 2A/2C receptor antagonist MDL 11,939". Neuroscience Research Communications. 35 (2): 83–95. :10.1002/nrc.20023.  1520-6769.
    5. Gudelsky, Gary A.; Yamamoto, Bryan; Nash, J. Frank (1994). "Potentiation of 3,4-methylenedioxymethamphetamine-induced dopamine release and serotonin neurotoxicity by 5-HT2 receptor agonists". European Journal of Pharmacology. 264 (3): 325–330. :10.1016/0014-2999(94)90669-6.  0014-2999.
    6. Capela, J. P.; Fernandes, E.; Remião, F.; Bastos, M. L.; Meisel, A.; Carvalho, F. (2007). "Ecstasy induces apoptosis via 5-HT2A-receptor stimulation in cortical neurons". Neurotoxicology. 28 (4): 868–875. :10.1016/j.neuro.2007.04.005.  0161-813X. PMID 17572501.
    7. Passie, T.; Halpern, J. H.; Stichtenoth, D. O.; Emrich, H. M.; Hintzen, A. "The Pharmacology of Lysergic Acid Diethylamide: A Review" (PDF). CNS Neuroscience & Therapeutics. 14: 295–314. :10.1111/j.1755-5949.2008.00059.x.  1755-5930. Archived from the original (PDF) on May 1, 2013. Retrieved January 1, 2020.
    8. Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. :10.1007/BF03161089.  1556-9039.
    9. "Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet" (in Danish). Lægemiddelstyrelsen [Danish Medicines Ageny]. August 31, 2015. Retrieved January 1, 2020.
    10. "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
    11. "Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (PDF). Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27 (in German). Bundesanzeiger Verlag. July 17, 2019. pp. 1083–1094. Retrieved January 1, 2020.
    12. "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
    13. "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). VSIA Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020.
    14. "31 nya substanser klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten [Public Health Agency of Sweden]. January 26, 2016. Retrieved January 1, 2020.
    15. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel,psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien: Änderung vom 2. November 2015" (PDF) (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
    16. "Karar Sayısı : 2016/8548" (PDF) (in Turkish). Resmi Gazete. Retrieved January 15, 2020.
    17. Advisory Council on the Misuse of Drugs (June 10, 2014). "Update of the generic definition for tryptamines" (PDF). Government Digital Service. p. 12. Retrieved January 1, 2020.

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

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