Ergocristine
Also known asErgocrystine · ergocrystin · ergokrystin · Ergocristin · ERGOCRISTINE [MI] · ERGOCRISTINE [WHO-DD]
(6aR,9R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
- PubChem CID
- 31116
- ChEMBL
- CHEMBL446315
- Measurements
- 3
- InChIKey
- HEFIYUQVAZFDEE-MKTPKCENSA-N
I · Summary
What is known
Published passages, each quoted whole and attributed to the database that published it. Two blocks are written here rather than quoted, and both say so where they stand: the synthesized summary at the top, which may draw only on the passages beneath it, and the history note, which cites the works it came from. Every claim in either carries a marker to its source.
What it is
Ergocristine is ergotaman bearing benzyl, hydroxy, and isopropyl groups at the 5', 12' and 2' positions, respectively, and oxo groups at positions 3', 6', and 18. It is a natural ergot alkaloid. It derives from a hydride of an ergotaman.
ergocristine has been reported in Claviceps grohii, Calamagrostis arundinacea, and other organisms with data available.
Ergocristine is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. Ergocristine is one of 3 similar peptides referred to as ergotoxine alkaloids, the other two being ergocryptine and ergocornine. Ergotoxines prepared into their hihydroergotoxine mesylates, commonly known as ergoloid mesylates, are used in the symptomatic therapy of age-related dementia. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (L1918, A2915)
an ergot alkaloid; one of the three components of ergotoxine; has alpha blocking action, stimulates smooth muscles & antagonizes serotonin; used as oxytocic & in peripheral disorders; minor descriptor (77-86); on-line & INDEX MEDICUS search EROLINES (77-86); RN given refers to ((5'alpha)-isomer)
Recognized use
Ergocristine and its salts (DEA Code Number: 8612) are List I Chemicals regulated by the Controlled Substances Act.
Hazardous Substances Data Bank (HSDB)21 CFR 1310.02(a) (30) (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2017: https://www.ecfr.gov
List I chemical means a chemical specifically designated by the Administrator in section 1310.02(a) of this chapter that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance.
Hazardous Substances Data Bank (HSDB)21 CFR 1300.02 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2017: https://www.ecfr.gov
This rulemaking finalizes a February 24, 2010, Notice of Proposed Rulemaking in which DEA proposed to control the chemical precursor ergocristine as a List I chemical under the Controlled Substances Act (CSA). Clandestine laboratories are using this chemical as a substitute for the List I chemicals ergotamine and ergonovine to illicitly manufacture the schedule I controlled substance lysergic acid diethylamide (LSD).
Hazardous Substances Data Bank (HSDB)US DOJ/DEA; Control of Ergocristine, a Chemical Precursor Used in the Illicit Manufacture of Lysergic Acid Diethylamide, as a List I Chemical (21 CFR Part 1310, Docket No. DEA-320F), Federal Register: Marcy 31, 2011. Available from, as of July 13, 2017: https://www.deadiversion.usdoj.gov/fed_regs/rules/2011/fr0331.htm
... In the rat, ergocristine acts as an alpha 2-adrenoceptors agonist, and an alpha 1-adrenoceptors antagonist.
Hazardous Substances Data Bank (HSDB)PMID 2822556Roquebert J, Demichel P; Fundam Clin Pharmacol 1 (1): 23-33 (1987)
How it acts
(1) The action of ergocristine at alpha-adrenoceptors was studied in vivo in the pithed rat, and in vitro on the rat isolated vas deferens. (2) In the pithed rat, the pressor response to ergocristine was reduced competitively by yohimbine, but not by prazosin. (3) Ergocristine decreased the tachycardia elicited by electrical stimulation of the cardioaccelerator sympathetic nerves, this effect being antagonized by yohimbine. (4) At postsynaptic alpha 1-adrenoceptors, on the vas deferens of the rat, ergocristine antagonized the contraction induced by phenylephrine in a competitive manner (pA2 = 7.85). (5) These results show that vasoconstriction due to ergocristine is mediated by alpha 2-adren…
Hazardous Substances Data Bank (HSDB)PMID 2822556Roquebert J, Demichel P; Fundam Clin Pharmacol 1 (1): 23-33 (1987)
Behavior carries the pharmacological classes and the acute-effect durations, with plasma half-life kept separate from duration of effect.
History, discovery and cultural use
— Not in this archive. PubChem, ChEMBL and the Human Protein Atlas publish pharmacology, regulation and toxicology, and none of them publishes a heading for when Ergocristine was first made, by whom, or how it has been used. That is a gap in the databases this site reads and not a gap in the literature — the history of these compounds is written, at length and under peer review, in the works below. This site does not summarize them; it says where they are. Where a published passage above happens to touch origin or traditional use, it appears inside the entry that carries it.
Histories of this field
Scholarship on psychedelics generally, not on Ergocristine specifically. Whether any of these treats this compound is a question for the book, not for this page.
Mescaline: A Global History of the First Psychedelic
Traces mescaline and the peyote and San Pedro cacti from pre-Columbian ritual use through nineteenth-century chemistry to twentieth-century psychiatry and the counterculture.
Jay M. Mescaline: A Global History of the First Psychedelic. Yale University Press, New Haven and London; 2019. ISBN 9780300231076.
Expanding Mindscapes: A Global History of Psychedelicsopen access
Essays on the international and cross-cultural history of psychedelic science, deliberately decentring the standard North American and European account.
Dyck E, Elcock C, editors. Expanding Mindscapes: A Global History of Psychedelics. The MIT Press, Cambridge MA; 2023. ISBN 9780262546935 (paper), 9780262376891 (open access). doi:10.7551/mitpress/14417.001.0001.
Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers
Botany, ethnography and chemistry of the principal hallucinogenic plants, by the founder of modern ethnobotany and the chemist who first synthesized LSD.
Schultes RE, Hofmann A, Rätsch C. Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers. 2nd ed. Healing Arts Press, Rochester VT; 2001. ISBN 9780892819799.
Psychonauts: Drugs and the Making of the Modern Mind
The tradition of scientific self-experimentation with psychoactive drugs, and its part in the emergence of psychology and of modernism.
Jay M. Psychonauts: Drugs and the Making of the Modern Mind. Yale University Press, New Haven; 2023. ISBN 9780300257946.
Ancient Psychoactive Substances
Archaeological and bioarchaeological evidence for psychoactive plant use across the ancient world.
Fitzpatrick SM, editor. Ancient Psychoactive Substances. University Press of Florida, Gainesville; 2018. ISBN 9780813056708.
A chapter tracing psychedelic and entactogen research from earlier ritual use through the mid-century research period to current clinical trials.
Stroud C, Posey Norris SM, Matney C, editors. History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders. In: Exploring Psychedelics and Entactogens as Treatments for Psychiatric Disorders: Proceedings of a Workshop. National Academies Press, Washington DC; 2022. NBK587225.
Workshop proceedings record what participants said; they are not a consensus statement of the National Academies.
Peer-reviewed review covering the isolation, synthesis, pharmacology and ritual use of peyote and mescaline.
Dinis-Oliveira RJ, Pereira CL, da Silva DD. Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions. Current Molecular Pharmacology 12(3):184–194; 2019. doi:10.2174/1874467211666181010154139.
Institutional archives
- Heffter Research Institute Funds and coordinates clinical research on psilocybin, and keeps records of the studies it has supported since 1993. Sponsors the research it archives.
- Multidisciplinary Association for Psychedelic Studies (MAPS) Sponsors clinical research, chiefly on MDMA-assisted therapy, and publishes an archive of historical and contemporary documents. A sponsor and an advocacy organization, not a disinterested archive; its clinical programme has a commercial arm.
The rest of this dossier
- Affinity — 3 measurements in this archive, equilibrium constants kept apart from functional readouts.
- Toxicology — 3 published passages, plus any assay in this archive bearing on toxicity.
- Legal — listed by the DEA among its drugs of concern, with no schedule stated in the record held here.
- Systems — where this compound’s targets are transcribed, by brain region and tissue.
Passages via PubChem descriptive sections, aggregating DrugBank, LiverTox, FDA, DEA, HSDB, EPA. Each is quoted whole and attributed to the database that published it. The only prose written here about Ergocristine is the history note, which says so on its face and carries a reference for every claim in it.
II · Identity
Structure and descriptors
Descriptors are computed here with RDKit from the structure PubChem returns — not from the archive's stored copy, so an edited local structure cannot reach this table.
- Formula
- C35H39N5O5R
- Molecular weight
- 609.73g/molR
- Exact mass
- 609.2951DaR
- cLogP
- 2.63R
- TPSA
- 118.2ŲR
- H-bond donors
- 3R
- H-bond acceptors
- 6R
- Rotatable bonds
- 5R
- Aromatic rings
- 3R
- Heavy atoms
- 45R
- Fraction sp³
- 0.457R
- Formal charge
- 0R
Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.
Bemis–Murcko scaffold
O=C(NC1OC2[C@@H]3CCCN3C(=O)[C@H](Cc3ccccc3)N2C1=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2NC1
Shared with Ergotamine. All families
III · Behavior
Behavioral summary
Class, mechanism, and the duration of acute effects — each quoted from the record or trial that publishes it. Duration of effects and plasma half-life are shown separately, because they are different quantities and diverge by a factor of three or four.
Classification
Duration of acute subjective effects
—
No controlled human trial reporting a duration for this compound is cited here. The archive holds no other record of one either. A duration is not inferred from a chemical relative.
Plasma elimination half-life
How fast the body clears the drug — not how long the effects last. The two diverge sharply: LSD is cleared with a half-life of about 2.6 h while its subjective effects run 8–12 h.
Male rats in which three pituitaries were grafted beneath the kidney capsule showed approximately a fourfold increase in circulating plasma prolactin concentration. The elevated plasma prolactin concentration did not remain at a constant level but fluctuated with time. The elevated prolactin concentration declined immediately after a sing…
Hazardous Substances Data Bank (HSDB)PMID 42476Shin SH; Can J Physiol Pharmacol 57 (11): 1313-6 (1979)
Primary pharmacological drivers
ChEMBL holds no curated mechanism-of-action record for this compound. The measured affinities below are the evidence this archive has for what it binds.
Mechanism, as published
Quoted verbatim from the database named after each passage, never summarized.
(1) The action of ergocristine at alpha-adrenoceptors was studied in vivo in the pithed rat, and in vitro on the rat isolated vas deferens. (2) In the pithed rat, the pressor response to ergocristine was reduced competitively by yohimbine, but not by prazosin. (3) Ergocristine decreased the tachycardia elicited by electrical stimulation o…
Hazardous Substances Data Bank (HSDB)PMID 2822556Roquebert J, Demichel P; Fundam Clin Pharmacol 1 (1): 23-33 (1987)
IV · Clinical
Clinical description
Where this compound's substance class sits in ICD-11 and DSM-5-TR, and how much of the recorded literature speaks to each domain of a mental status examination.
No diagnostic chapter is shown for this compound. Either PubChem records no MeSH pharmacological class for it, or the class it records is not one of the substance classes ICD-11 gives a chapter to. Inferring a chapter from the compound’s name or its binding profile would be a diagnosis this archive is in no position to make.
How much has been written about each domain
The clinical domains, and how many of the records this archive holds for this compound say something under each. What the terms mean, and the word list behind every spoke, are set out in the method.
- Perception 1
- matched on “hallucinat” · in Toxicology: Toxin and Toxin Target Database (T3DB)
- Cognition 2
- matched on “concentrat” · in PMID 42476; Toxicology: Hazardous Substances Data Bank (HSDB)
V · Systems
Systems physiology
Where the targets this compound binds are transcribed — brain regions on the left, peripheral and autonomic tissues on the right. A join of two measurements, not a claim about what the compound does to either.
Brain
basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.
Measured but not drawn — this anatomogram has no outline for them: pituitary gland 56.6, midbrain 23.4, retina 10.8, spinal cord 0.8.
Body
Square-root ramp · shared scale across both plates
Shading is transcript level — not affinity, and not affinity combined with expression. Outlined but unshaded organs hold none of this compound’s resolved targets above the atlas’s detection threshold. Anatomy from EMBL-EBI Anatomogram (Apache License 2.0); regions identified by Uberon (uberon.org), CC BY 3.0.
Brain regions
Regions where this compound's measured targets are transcribed. Linked from the plate above.
basal ganglia
62.0 nTPMpituitary gland
56.6 nTPMmidbrain
23.4 nTPMhypothalamus
10.8 nTPMretina
10.8 nTPMcerebral cortex
4.6 nTPMamygdala
3.4 nTPMhippocampal formation
2.1 nTPMcerebellum
0.8 nTPMspinal cord
0.8 nTPM
Peripheral & autonomic
Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.
salivary gland
11.3 nTPM- D2DRD28.9 pX11.3
adrenal gland
7.9 nTPMsmooth muscle
1.4 nTPMkidney
1.2 nTPMliver
1.0 nTPM- D1DRD17.3 pX1.0
skeletal muscle
0.8 nTPM- D2DRD28.9 pX0.8
lung
0.7 nTPMurinary bladder
0.7 nTPMcolon
0.4 nTPMsmall intestine
0.3 nTPMpancreas
0.2 nTPM- D2DRD28.9 pX0.2
stomach 1
0.2 nTPMheart muscle
0.1 nTPM- D2DRD28.9 pX0.1
duodenum
0.1 nTPM- D1DRD17.3 pX0.1
thyroid gland
0.1 nTPM- D1DRD17.3 pX0.1
spleen
0.1 nTPM- D1DRD17.3 pX0.1
Each row joins two published measurements and nothing else: the affinity this archive holds for the compound at that target, and the transcript level the Human Protein Atlas reports for that target’s gene in that region. Bars scale with expression only. Expression is not activation — a receptor transcribed in a region is a receptor available to be bound there, which is a weaker and more defensible claim than saying the region is affected.
Expression data from Human Protein Atlas (CC BY-SA 3.0), RNA expression, nTPM (normalized transcripts per million), consensus tissue dataset. Uhlén M, et al. Tissue-based map of the human proteome. Science. 2015;347(6220):1260419.
VI · Profile
Affinity rosette
The strongest measurement at each of 2 molecular targets. Cell-line and whole-organism screens are excluded here — they carry no affinity — and appear in the table below.
VII · Toxicology
Toxicological profile
What has been measured, and what has been published — kept apart, and neither scored. There is no risk rating on this page; the archive once carried one, identical for every compound, produced by a stub.
Measured in this archive
Assays that bear on toxicity, drawn from the same ChEMBL records as everything else on this page. They are measurements of what a compound binds or does to cells — not verdicts about what it does to a person.
No hERG, cytochrome, cytotoxicity or transport measurement exists for Ergocristine in this archive.
As published
Quoted verbatim from the database named after each passage, never summarized — a summary of a toxicology statement is a new claim.
Toxicity Summary
IDENTIFICATION AND USE: Ergocristine is a solid. Ergocristine and its salts are List I Chemicals. Clandestine laboratories are using this chemical as a substitute for the List I chemicals ergotamine and ergonovine to illicitly manufacture the schedule I controlled substance lysergic acid diethylamide (LSD). HUMAN STUDIES: Of all tested ergot alkaloids, ergocristine was the most cytotoxic compound inducing apoptosis i…
Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity tow…
Human Toxicity Excerpts
/ALTERNATIVE and IN VITRO TESTS/ Ergot alkaloids are secondary metabolites produced by fungi of the species Claviceps. Toxic effects after consumption of contaminated grains are described since Medieval times. Of the more than 40 known ergot alkaloids six are found predominantly. These are ergotamine, ergocornine, ergocryptine, ergocristine, ergosine and ergometrine, along with their corresponding isomeric forms (-in…
Hazardous Substances Data Bank (HSDB)PMID 21295106Mulac D, Humpf HU; Toxicology 282 (3): 112-21 (2011)
Published passages via PubChem toxicology sections, aggregating Hazardous Substances Data Bank (HSDB), RTECS, LiverTox. No figure on this page is scored, ranked or combined into a risk level.
VIII · Evidence
Every measurement
One row per published value. The identifier in the last column resolves to the ChEMBL assay record it was read from.
Equilibrium binding constants 2
Ki and Kd — a concentration at equilibrium. Directly comparable across rows at the same target.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| D2 | Dopamine receptors | Ki | 1.40 | 8.85 | CALF | PMID 995128 |
| D1 | Dopamine receptors | Ki | 52.00 | 7.28 | CALF | PMID 995128 |
Functional readouts 1
IC₅₀, EC₅₀, AC₅₀ and potency. Assay-dependent, and not interchangeable with a binding constant.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| Microtubule-associated protein tau | Unclassified | Potency | 12,589 | 4.90 | Homo sapiens | CHEMBL1614421 |
- P
- PubChem
- C
- ChEMBL
- R
- Computed here with RDKit
- D
- Derived here from the stored measurement
IX · Trials
Registered clinical trials
Studies filed with ClinicalTrials.gov that name this compound as an intervention. A registered trial is a protocol, not a result — status and enrollment are printed beside every row, and withdrawn studies are counted rather than hidden.
— No registered study names Ergocristine as an intervention. That is an absence of registered research, not evidence about the compound. Most of this archive has never been the subject of a registered trial.
Records from ClinicalTrials.gov (U.S. National Library of Medicine, NIH), API v2. A study is listed against a compound only when a verified name for that compound appears as a whole word in one of the study's own intervention names. A short code must appear as written, and a name the registry uses for something else (Aleph, a vaccine maker) is not matched. Title matches are not accepted. The matched name and the intervention text it matched are shown with every row.
Searched as Ergocristine · Ergocrystine · ergocrystin. Run this search at the registry.
A registered trial is a protocol somebody filed with the registry. It is not a result, and nothing on this plate says whether Ergocristine worked.
X · Legal
Controlled-substance status
United States federal scheduling, read from the DEA records this archive holds and shown with the passage each was read from. Not legal advice, and not necessarily current.
As the DEA states it
Quoted whole. The badge above is a reading of these passages and adds nothing to them.
List I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)
Drug Enforcement Administration (DEA)21 CFR Section 1310.02(a) https://www.ecfr.gov/current/title-21/chapter-II/part-1310/section-1310.02
Other regulatory records
Registers outside the DEA that hold an entry for Ergocristine — chemical-safety and national inventories, each naming itself. They are not scheduling decisions.
The following chemicals have been specifically designated by the Administrator of the Drug Enforcement Administration as the listed chemicals subject to the provisions of this part and parts 1309 and 1313 of this chapter. Each chemical has been assigned the DEA Chemical Code Number set forth opposite it. Ergocristine and its salts (DEA Code: 8612) is included on this list.
Hazardous Substances Data Bank (HSDB)21 CFR 1310.02(a) (30) (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2017: https://www.ecfr.gov
United States federal status only. State law differs, and so does the law of every other country — none of it is represented here. Scheduling changes, and this reflects the DEA records held by PubChem descriptive sections when the monograph was last harvested, not necessarily today. This is a record of what a database publishes, not legal advice.
XI · Literature
Sources behind this dossier
The papers this compound's values were read from, ranked by what each contributed. Not a review of the field.
Every paper below is one some value on this page came from — a binding constant, a passage of pharmacology or toxicology, or a measured duration. Each entry says what this archive took from it. Nothing else is claimed about any of them: the title is the study’s own account of itself, and a summary written here would be an assertion with no source behind it.
- 01
Burt DR, Creese I, Snyder SH · Molecular pharmacology 1976
- · 2 measurements at 2 targets (Ki), strongest D2 at 8.85 pX
- 02
Cytotoxicity and accumulation of ergot alkaloids in human primary cells
Mulac D, Humpf HU · Toxicology 2011
- · Human Toxicity Excerpts
- 03
Agonist/antagonist activity of ergocristine at alpha-adrenoceptors in the rat
Roquebert J, Demichel P · Fundamental & clinical pharmacology 1987
- · Mechanism of Action
- 04
Shin SH · Canadian journal of physiology and pharmacology 1979
- · Biological Half-Life