Ergine: Difference between revisions

{{Short description|Chemical compound}}

{{More citations needed|date=July 2007}}

{{Drugbox | Watchedfields = changed

| verifiedrevid = 443731816

| image = Ergine.svg

| width =

| image2 = D-lysergic_acid_amide_anim.gif

| width2 =

<!--Clinical data-->

| pregnancy_category = X<ref>{{citation |url=http://www.erowid.org/plants/morning_glory/morning_glory_basics.shtml |title=Erowid Morning Glory Basics |publisher=Erowid.org |access-date=2012-02-03}}</ref>

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->

| legal_BR = F2

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_DE = NpSG

| legal_NZ = <!-- Class A, B, C -->

| legal_UK = Class A

| legal_US = Schedule III

| legal_status = Illegal in France<ref>{{cite web|date=20 May 2021|title=Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants|url=https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554|website=www.legifrance.gouv.fr|language=fr}}</ref>

| routes_of_administration = [[Oral administration|Oral]], [[intramuscular injection]]

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound =

| metabolism = Hepatic

| elimination_half-life =

| excretion = Renal

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 073830XH10

| PubChem = 442072

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 227213

| synonyms = LSA; d-Lysergic acid amide; d-Lysergamide; Ergine; LA-111

<!--Chemical data-->

| SMILES = O=C(N)[C@@H]1C=C2C3=CC=CC4=C3C(C[C@@]2([H])N(C1)C)=CN4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GENAHGKEFJLNJB-QMTHXVAHSA-N

<!--Physical data-->

| melting_point = 135

| melting_notes = Decomposes<ref>{{cite journal| vauthors = Smith S, Timmis GM |title=98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine|journal=Journal of the Chemical Society (Resumed)|date=1932|pages=763|doi=10.1039/jr9320000763}}</ref>

}}

'''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 [[Turbina corymbosa|ololiuhqui]], [[Argyreia nervosa|Hawaiian baby woodrose]] and [[Ipomoea tricolor|morning glories]] have been linked to ergine and/or isoergine, its [[epimer]], as it is an alkaloid present in the seeds.<ref>{{Cite journal|vauthors=Perrine DM|date=2000|title=Mixing the Kykeon|url=http://www.psychedelic-library.org/Mixing%20the%20Kykeon%20Final%20Draft.pdf|journal=ELEUSIS: Journal of Psychoactive Plants and Compounds|volume=New Series 4|pages=9|access-date=2008-05-05|archive-date=2019-07-20|archive-url=https://web.archive.org/web/20190720192225/http://www.psychedelic-library.org/Mixing%20the%20Kykeon%20Final%20Draft.pdf|url-status=dead}}</ref><ref name="erowid3">{{citation|author=Alexander Shulgin|title=TiHKAL|chapter=#26. LSD-25|chapter-url=http://www.erowid.org/library/books_online/tihkal/tihkal26.shtml|publisher=Erowid.org|access-date=2012-02-03}}</ref><ref name="LSD my problem child4">{{cite book| vauthors = Hofmann A |title=LSD My Problem Child: Reflections on Sacred Drugs, Mysticism, and Science |date=2009 |publisher=MAPS.org |isbn=978-0979862229 |edition=4th}}</ref>

==Occurrence in nature==

Ergine has been found in high concentrations of 20&nbsp;μg/g dry weight in the [[Stipa robusta|sleepygrass]] infected with an ''[[Acremonium]]'' [[Endophyte|endophytic]] [[fungus]] together with other ergot alkaloids.<ref>{{cite journal | vauthors = Petroski RJ, Powell RG, Clay K | title = Alkaloids of Stipa robusta (sleepygrass) infected with an Acremonium endophyte | journal = Natural Toxins | volume = 1 | issue = 2 | pages = 84–88 | year = 1992 | pmid = 1344912 | doi = 10.1002/nt.2620010205 | url = http://www3.interscience.wiley.com/cgi-bin/abstract/112640007/ABSTRACT | url-status = dead | archive-url = https://archive.today/20121216154924/http://www3.interscience.wiley.com/cgi-bin/abstract/112640007/ABSTRACT | archive-date = 2012-12-16 }}</ref>

Ergine is a component of the alkaloids contained in the [[Claviceps purpurea|ergot]] fungus, which grows on the heads of infected rye grasses.

It is also found in the seeds of several varieties of [[Morning glory|morning glories]] in concentrations of approximately 10&nbsp;μg per seed, as well as [[Hawaiian baby woodrose]] seeds, at a concentration of around 0.13% of dry weight.<ref name=":03">{{cite journal | vauthors = Chao JM, Der Marderosian AH | title = Ergoline alkaloidal constituents of Hawaiian baby wood rose, Argyreia nervosa (Burm. f.) Bojer | journal = Journal of Pharmaceutical Sciences | volume = 62 | issue = 4 | pages = 588–591 | date = April 1973 | pmid = 4698977 | doi = 10.1002/jps.2600620409 }}</ref>

==History==

''Ololiuhqui'' was used by South American healers in shamanic healing ceremonies.<ref name="Unauthorized research on cluster headache3">{{cite journal| vauthors = Sewell RA |date=2008|title=Unauthorized research on cluster headache. |journal=The Entheogen Review |volume=16 |issue=4 |pages=117–125 | url = http://psychonautdocs.com/docs/sewell_2009_unauthorized_research_on_cluster_headache.pdf }}</ref> Similarly, ingestion of [[morning glory]] seeds by [[Mazatec]] tribes to "commune with their gods" was reported by [[Richard Evans Schultes|Richard Schultes]] in 1941 and is still practiced today.<ref>{{cite book| vauthors = Schultes RE |title=A Contribution to Our Knowledge of Rivea Corymbosa: The Narcotic Ololinqui of the Aztecs|date=1941|publisher=Botanical Museum of Harvard University|edition=1st}}</ref><ref name="Unauthorized research on cluster headache3"/>

Additional reports of the use of ergine were made by Don Thomes MacDougall. He reported that the seeds of ''[[Ipomoea violacea]]'' were used as [[sacrament]]s by certain [[Zapotec peoples|Zapotecs]], sometimes in conjunction with the seeds of ''[[Rivea corymbosa]]'', another species which has a similar chemical composition, with [[lysergol]] instead of [[ergometrine]].<ref name="LSD my problem child4"/>

Ergine was assayed for human activity by [[Albert Hofmann]] in self-trials in 1947, well before it was known to be a natural compound. [[Intramuscular]] administration of a 500 microgram dose led to a tired, dreamy state, with an inability to maintain clear thoughts. After a short period of sleep the effects were gone, and normal [[Baseline (pharmacology)|baseline]] was recovered within five hours.<ref name="erowid3"/>

In 1956, the [[Central Intelligence Agency]] conducted research on the psychedelic properties of the ergine in the seeds of ''Rivea corymbosa'', as Subproject 22 of [[MKULTRA]].<ref>{{cite web|title=PROJECT MKULTRA, SUBPROJECT 22 (W/ATTACHMENTS)|url=https://www.cia.gov/readingroom/document/0000707674|website=Central Intelligence Agency}}</ref>

In 1959, Hofmann was the first to isolate chemically pure ergine from the seeds of [[Turbina corymbosa]], determining that it, and other alkaloids, were acting as the main active components in the seeds.<ref name="LSD my problem child4"/> Twenty years prior to its isolation, ergine was first chemically defined by English chemists S. Smith and G. M. Timmis as the cleavage product of ergot alkaloids. Additionally, Guarin and Youngkin reportedly isolated the crude alkaloid in 1964 from morning glory seeds.<ref name="Groger Method">{{cite journal| vauthors = Der Marderosian AH, Guarino AM, De Feo JJ, Youngken Jr HW |date=1964|title=A Uterine Stimulant Effect of Extracts of Morning Glory Seeds|journal=Pschedelic Review|pages=317–323}}</ref>

==Ingestion==

Like other psychedelics, ergine is not considered to be addictive. Additionally, there are no known [[death]]s directly associated with [[Pharmacology|pharmacological]] effects of ergine consumption. All associated deaths are due to indirect causes, such as [[self-harm]], [[Judgement|impaired judgement]], and adverse [[drug interaction]]s. One known case involved a [[suicide]] that was reported in 1964 after [[ingestion]] of [[morning glory]] [[seeds]].<ref>{{cite journal | vauthors = Cohen S | title = Suicide Following Morning Glory Seed Ingestion | journal = The American Journal of Psychiatry | volume = 120 | issue = 1 | pages = 1024–1025 | date = April 1964 | pmid = 14138842 | doi = 10.1176/ajp.120.10.1024 }}</ref> Another instance is a death due to [[Falling (accident)|falling off]] of a [[building]] after ingestion of [[Argyreia nervosa|Hawaiian baby woodrose]] [[seed]]s and [[alcohol (drug)|alcohol]].<ref>{{cite journal | vauthors = Klinke HB, Müller IB, Steffenrud S, Dahl-Sørensen R | title = Two cases of lysergamide intoxication by ingestion of seeds from Hawaiian Baby Woodrose | journal = Forensic Science International | volume = 197 | issue = 1–3 | pages = e1–e5 | date = April 2010 | pmid = 20018470 | doi = 10.1016/j.forsciint.2009.11.017 }}</ref>

===Physiological effects===

While its physiological effects vary from person to person, the following symptoms have been attributed to the consumption of ergine or ergine containing seeds:<ref name="LSD my problem child4"/><ref name="Unauthorized research on cluster headache3"/><ref name=":12">{{cite journal | vauthors = Ingram AL | title = Morning Glory Seed Reaction | journal = JAMA | volume = 190 | issue = 13 | pages = 1133–1134 | date = December 1964 | pmid = 14212309 | doi = 10.1001/jama.1964.03070260045019 | edition = 13 }}</ref>

* [[Sedation]]

* Visual and auditory [[hallucination]]s

* [[Euphoria]]

* Loss of motor control

* [[Nausea]]

* [[Vasoconstriction]]

* [[Delusion]]

* [[Anxiety]]

* [[Paranoia]]

* [[Irregular heartbeat]]<ref name="Kremer_2012">{{cite journal | vauthors = Kremer C, Paulke A, Wunder C, Toennes SW | title = Variable adverse effects in subjects after ingestion of equal doses of Argyreia nervosa seeds | journal = Forensic Science International | volume = 214 | issue = 1–3 | pages = e6–8 | date = January 2012 | pmid = 21803515 | doi = 10.1016/j.forsciint.2011.06.025 | url = }}</ref>

* Sexual arousal<ref name="Subramoniam_2007">{{cite journal | vauthors = Subramoniam A, Madhavachandran V, Ravi K, Anuja VS | title = Aphrodisiac property of the elephant creeper Argyreia nervosa. | journal = Journal of Endocrinology and Reproduction | date = December 2007 | volume = 11 | issue = 2 | pages = 82–85 | url = https://indianjournalsonline.com/index.php/jer/article/view/2092 }}</ref>

* [[Tachycardia]]<ref name="Marneros_2006">{{cite journal | vauthors = Marneros A, Gutmann P, Uhlmann F | title = Self-amputation of penis and tongue after use of Angel's Trumpet | journal = European Archives of Psychiatry and Clinical Neuroscience | volume = 256 | issue = 7 | pages = 458–9 | date = October 2006 | pmid = 16783491 | doi = 10.1007/s00406-006-0666-2 | s2cid = 9261722 | url = }}</ref>

* [[Mydriasis]]<ref name="Marneros_2006"/>

* [[Hypertonia]]<ref name="Marneros_2006"/>

* Respiratory disturbances<ref name="Marneros_2006"/>

* [[Cramps]]<ref name="Marneros_2006"/>

One study found that 2 of 4 human subjects experienced cardiovascular dysregulation and the study had to be halted, concluding that the ingestion of seeds containing ergine was less safe then commonly believed. Importantly this may have been a product of other substances within the seeds. The same study also observed that reactions were highly differing in type and intensity between different subjects.<ref name="Kremer_2012"/> Another study in mice found that the drug had aphrodisiac properties, inducing increased sexual behavior.<ref name="Subramoniam_2007"/>

A study gave mice 3000&nbsp;mg/kg with no lethal effects.{{citation needed|date=February 2024}}

===Psychedelic component===

Ergine is thought to be a [[serotonergic psychedelic]] and its psychedelic effects are thought to be due to it being a [[partial agonist]] of the [[5-HT2A receptor|5-HT_2A receptor]]. Though, the reason as to why this may be hallucinogenic remains elusive.

The idea that ergine is the main psychedelic component in ergine containing seeds (morning glory, Hawaiian baby woodrose) is well debated, as the effects of isolated synthetic ergine are reported to be only mildly psychedelic.<ref name=":03"/><ref name=":12" /> Thus, the overall psychedelic experience after consumption of such seeds has been proposed to be due to a mixture of ergoline alkaloids.

==Pharmacology==

===Pharmacodynamics===

{| class="wikitable floatright"

|+ Affinities of LSA and LSD for various receptors<ref name="pmid23665164">{{cite journal | vauthors = Paulke A, Kremer C, Wunder C, Achenbach J, Djahanschiri B, Elias A, Schwed JS, Hübner H, Gmeiner P, Proschak E, Toennes SW, Stark H | display-authors = 6 | title = Argyreia nervosa (Burm. f.): receptor profiling of lysergic acid amide and other potential psychedelic LSD-like compounds by computational and binding assay approaches | journal = Journal of Ethnopharmacology | volume = 148 | issue = 2 | pages = 492–497 | date = July 2013 | pmid = 23665164 | doi = 10.1016/j.jep.2013.04.044 }}</ref>

|-

! rowspan="2" | Receptor !! colspan="2" | Affinity (K_i [nM])

|-

! LSA !! LSD

|-

| [[5-HT1A receptor|5-HT_1A]] || 10 || 2.5

|-

| [[5-HT2 receptor|5-HT₂]] || 28 || 0.87

|-

| [[D1 receptor|D₁]] || 832 || 87

|-

| [[D2L receptor|D_2L]] || 891 || 155

|-

| [[D2S receptor|D_2S]] || 145 || 25

|-

| [[D3 receptor|D₃]] || 437 || 65

|-

| [[D4.4 receptor|D_4.4]] || 141 || 30

|-

| [[α1-Adrenergic receptor|α₁]] || 912 || 60

|-

| [[α2-Adrenergic receptor|α₂]] || 62 || 1.0

|-

| colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' 5-HT_1A and D₁ are for pig receptors.<ref name="pmid23665164" />

|}

Ergine interacts with [[serotonin receptor|serotonin]], [[dopamine receptor|dopamine]], and [[adrenergic receptor]]s similarly to but with lower [[affinity (pharmacology)|affinity]] than [[lysergic acid diethylamide]] (LSD).<ref name="pmid23665164" /> The psychedelic effects of ergine can be attributed to activation of serotonin [[5-HT2A receptor|5-HT_2A receptor]]s.<ref name="HalberstadtNichols2020">{{cite book| vauthors = Halberstadt AL, Nichols DE |title=Handbook of the Behavioral Neurobiology of Serotonin|chapter=Serotonin and serotonin receptors in hallucinogen action|series=Handbook of Behavioral Neuroscience|volume=31|year=2020|pages=843–863|issn=1569-7339|doi=10.1016/B978-0-444-64125-0.00043-8|isbn=9780444641250}}</ref>

==Chemistry==

===Biosynthesis===

[[File:Ergine_biosynthesis_part_1_(fixed).png|border|center|800x800px|Biosynthesis of the ergoline scaffold]]

The biosynthetic pathway to ergine starts like most other ergoline alkaloid- with the formation of the ergoline scaffold. This synthesis starts with the [[prenylation]] of L-tryptophan in an SN1 fashion with [[dimethylallyl diphosphate]] (DMAPP) as the prenyl donor and catalyzed by prenyltransferase 4-dimethylallyltryptophan synthase (DMATS), to form 4-L-dimethylallyltryptophan (4-L-DMAT). The DMAPP is derived from [[mevalonic acid]]. A three strep mechanism is proposed to form 4-L-DMAT: the formation of an allylic [[carbocation]], a nucleophilic attack of the [[indole]] nucleus to the cation, followed by deprotonation to restore aromaticity and to generate 4-L-DMAT.<ref name=":2">{{cite journal | vauthors = Gerhards N, Neubauer L, Tudzynski P, Li SM | title = Biosynthetic pathways of ergot alkaloids | journal = Toxins | volume = 6 | issue = 12 | pages = 3281–3295 | date = December 2014 | pmid = 25513893 | pmc = 4280535 | doi = 10.3390/toxins6123281 | doi-access = free }}</ref> 4-Dimethylallyltyptophan [[N-methyltransferase|''N''-methyltransferase]] (EasF) catalyzes the ''N''-methylation of 4-L-DMAT at the amino of the tryptophan backbone, using [[S-Adenosyl methionine]] (SAM) as the methyl source, to form 4-dimethylallyl-L-abrine (4-DMA-L-abrine).<ref name=":2" /> The conversion of 4-DMA-L-abrine to [[Chanoclavine|chanoclavine-I]] is thought to occur through a decarboxylation and two oxidation steps, catalyzed by the [[FAD dependent oxidoreductase family|FAD dependent oxidoreductase]], EasE, and the [[catalase]], EasC. The chanoclavine intermediate is then oxidized to chanoclavine-l-aldehyde, catalyzed by the [[short-chain dehydrogenase/reductase]] (SDR), EasD.<ref name=":2" /><ref name=":3">{{Cite journal| vauthors = Willingale J, Atwell SM, Mantle PG |date=1983-07-01|title=Unusual Ergot Alkaloid Biosynthesis in Sclerotia of a Claviceps purpurea Mutant|journal=Microbiology|volume=129|issue=7|pages=2109–2115|doi=10.1099/00221287-129-7-2109|issn=1350-0872|doi-access=free}}</ref>

[[File:Ergine_biosynthesis_part_2.png|border|center|650x650px|Formation of argoclavine]]

From here, the biosynthesis diverges and the products formed are plant and fungus-specific. The biosynthesis of ergine in [[Claviceps purpurea|C''laviceps purpurea'']] will be exemplified, in which [[agroclavine]] is produced following the formation of chanoclavine-l-aldehyde, catalyzed by EasA through a keto-enol [[tautomerization]] to facilitate rotation about the C-C bond, followed by tautomerization back to the aldehyde and condensation with the proximal secondary amine to form an iminium species, which is subsequently reduced to the tertiary amine and yielding argoclavine.<ref name=":2" /><ref name=":3" /> [[Cytochrome P450 monooxygenase]]s (CYP₄₅₀) are then thought to catalyze the formation of [[elymoclavine]] from argoclavine via a 2 electron oxidation. This is further converted to paspalic acid via a 4 electron oxidation, catalyzed by ''cloA'', a CYP₄₅₀ monooxygenase. Paspalic acid then undergoes [[isomerization]] of the C-C double bond in conjugation with the acid to form [[Lysergic acid|D-lysergic acid]].<ref name=":2" /> While the specifics of the formation of ergine from [[Lysergic acid|D-lysergic acid]] are not known, it is proposed to occur through a [[nonribosomal peptide synthase]] (NRPS) with two enzymes primarily involve: D-lysergyl peptide synthase (LPS) 1 and 2.<ref name=":2" /><ref name=":3" />

[[File:Ergine_biosynthesis_part_3.png|border|center|850x850px]]

==Legal status==

The legality of consuming, cultivating, and possessing ergine varies depending on the country.

There are no laws against possession of ergine-containing seeds in the United States. However, possession of the pure compound without a prescription or a DEA license would be prosecuted, as ergine, under the name "lysergic acid amide", is listed under Schedule III of the [[Controlled Substances Act]].<ref>{{Cite web|title=Initial schedules of controlled substances (Schedule III), Section 812|url=https://www.deadiversion.usdoj.gov/21cfr/21usc/812.htm|website=www.deadiversion.usdoj.gov|access-date=2020-01-17|archive-date=2021-11-04|archive-url=https://web.archive.org/web/20211104092917/https://www.deadiversion.usdoj.gov/21cfr/21usc/812.htm|url-status=dead}}</ref> Similarly, ergine is considered a Class A substance in the United Kingdom, categorized as a precursor to [[LSD]].

In most Australian states, the consumption of ergine containing materials is prohibited under state legislation.

In Canada, ergine is not illegal to possess as it is not listed under Canada's [[Controlled Drugs and Substances Act]], though it is likely illegal to sell for human consumption.<ref>{{Cite web|title=Erowid LSA Vault : Legal Status|url=https://erowid.org/chemicals/lsa/lsa_law.shtml|website=erowid.org|access-date=2020-05-05}}</ref>

In New Zealand, ergine is a controlled drug, however the plants and seeds of the morning glory species are legal to possess, cultivate, buy, and distribute.

== See also ==

*[[Argyreia nervosa]]

* [[List of entheogenic/hallucinogenic species]]

* [[List of psychoactive plants]]

* [[Tlitliltzin]] (''Ipomoea violacea'')

== References ==

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite book | vauthors = Powell W |author-link=William Powell (author) |title=The Anarchist Cookbook |publisher=Ozark Press |year=2002 |page=[https://archive.org/details/anarchistcookboo00powe/page/n41 44] |isbn=978-0-8488-1130-3|title-link=The Anarchist Cookbook }}

* {{cite journal |title=98. The Alkaloids of Ergot. Part III. Ergine, a New Base obtained by the Degradation of Ergotoxine and Ergotinine |journal=[[J. Chem. Soc.]] |year=1932 | vauthors = Sydney S, Timmis GM |volume=1932 |pages=763–766 |doi=10.1039/JR9320000763}}

* {{cite journal | vauthors = Juszczak GR, Swiergiel AH | title = Recreational use of D-lysergamide from the seeds of Argyreia nervosa, Ipomoea tricolor, Ipomoea violacea, and Ipomoea purpurea in Poland | journal = Journal of Psychoactive Drugs | volume = 45 | issue = 1 | pages = 79–93 | date = 2013-01-01 | pmid = 23662334 | doi = 10.1080/02791072.2013.763570 | s2cid = 22086799 }}

* {{cite journal | vauthors = Burillo-Putze G, López Briz E, Climent Díaz B, Munné Mas P, Nogue Xarau S, Pinillos MA, Hoffman RS | title = [Emergent drugs (III): hallucinogenic plants and mushrooms] | journal = Anales del Sistema Sanitario de Navarra | volume = 36 | issue = 3 | pages = 505–518 | date = 2013-09-01 | pmid = 24406363 | doi = 10.4321/s1137-66272013000300015 | doi-access = free }}

{{refend}}

* [http://www.erowid.org/plants/mushrooms/references/other/1971_hofmann_bulletin-narcotics.shtml Hofmann, A. ''Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico'' Bulletin on Narcotics 1971 1 3]

* [http://www.erowid.org/chemicals/lsa/lsa.shtml LSA Vault] – [[Erowid]]

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