LSA

(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

Overview

LSA belongs to Psychedelics / Ergolines.

Key safety note: LSA is an ergoline and shares ergot-type risks: it causes peripheral vasoconstriction, so cardiovascular disease, hypertension and pregnancy (ergot alkaloids stimulate the uterus) are important cautions.[3][2]
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology, mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or desirable outcomes.
  • Predominantly sedating and dream-like rather than brightly visual: often described as LSD's 'sleepy' cousin: drowsiness, a heavy body and dreamy, introspective mentation.
  • Common physical effects: nausea and vomiting (partly from other seed constituents), pronounced vasoconstriction with cold or tingling extremities, dizziness and motor incoordination.
  • Milder and less reliable perceptual and visual changes than LSD. Anxiety and unpleasant dysphoria are relatively common, especially from crude seed preparations.
  • Onset is roughly 0.5–3 hours and effects last about 4–10 hours.
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a “safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start low, go slow, wait for full effects before redosing, and never assume an unknown product matches these figures. Missing data is not evidence of safety.

Oral. Not a recommendation. LSA is almost always taken as morning glory or Hawaiian baby woodrose seeds, whose alkaloid content varies enormously between seeds, cultivars and batches. The seeds also contain other ergot alkaloids and are often coated with fungicides or insecticides that add toxicity. Vasoconstriction is a genuine risk. Seed-count figures are rough guides only.

Dose ranges

Pure LSA (approx.)

≈0.5–2 mg

Hawaiian baby woodrose seeds

≈5–10 seeds

Morning glory seeds

≈150–200 seeds

Duration

onset

≈0.5–3 h

total

≈4–10 h

Chemical & Physical Properties
FormulaC16H17N3O
Molar mass267.33 g/mol
StateSolid
Melting point135 °C (decomposes)
Boiling pointunavailable: true. reason: the compound decomposes at its melting point rather than boiling. No experimental boiling point is reported
Densityunavailable: true. reason: no reliable experimental value is reported for the solid
Vapor pressureNot reported
pKaNot reported
LogP1.6 (predicted, XLogP3)
SolubilityNot reported
Refractive indexNot reported
Identifiers & Synonyms
CAS478-94-4
CAS (enantiomer)
PubChem CID442072
InChIKeyGENAHGKEFJLNJB-QMTHXVAHSA-N
InChIInChI=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
SMILESCN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N

Synonyms

    Pharmacodynamics & Biochemistry

    LSA (ergine, d-lysergic acid amide) is the simple carboxamide of lysergic acid: structurally LSD without its two ethyl groups. Like LSD it is an agonist at serotonin 5-HT2A (and 5-HT2B) receptors, the action underlying its psychedelic effects, but it binds and activates them much less potently (roughly 30–120× lower 5-HT2A affinity than LSD) and with somewhat lower efficacy. It also has appreciable affinity for 5-HT1A, dopamine D1–D4 and α1/α2-adrenergic receptors: again weaker than LSD across the board, giving a broad but blunted ergoline profile. Its subjective character is notably more sedating and less visual than LSD, and its strong α-adrenergic and ergoline activity drives peripheral vasoconstriction. Albert Hofmann, who self-experimented with it, described a tired, dreamy, 'narcotic' state rather than a bright psychedelic one. LSA is the principal psychoactive alkaloid of morning glory (Ipomoea, Turbina/Rivea corymbosa: ololiuqui) and Hawaiian baby woodrose (Argyreia nervosa) seeds. Chemically it is a hydrolysis product of larger ergot alkaloids rather than a biosynthetic endpoint.

    Biological targets

    • 5-HT2A
    • 5-HT1A
    • 5-HT2C
    • 5-HT2B
    • D2
    • alpha1
    • alpha2

    Binding & functional measurements

    TargetMeasurementSpecies
    5-HT2BEC50 115 nMHuman
    5-HT2CKi 798 nMHuman
    5-HT1A receptorKi 10 nMPig
    5-HT2A receptorKi 28 nMUnspecified
    D1 receptorKi 832 nMUnspecified
    D2 receptorKi 891 nMUnspecified
    D3 receptorKi 437 nMUnspecified
    D4 receptorKi 141 nMUnspecified
    α1-adrenoceptorKi 912 nMUnspecified
    α2-adrenoceptorKi 62 nMUnspecified
    Pharmacokinetics
    BioavailabilityOrally active
    TmaxNot reported
    Half-lifeNot established in humans
    VdNot reported
    Protein bindingNot reported
    MetabolismHepatic
    ExcretionRenal
    Toxicology & Safety
    Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual health factors. Missing harms should never be interpreted as evidence of safety.

    Not reported

    LSA is an ergoline and shares ergot-type risks: it causes peripheral vasoconstriction, so cardiovascular disease, hypertension and pregnancy (ergot alkaloids stimulate the uterus) are important cautions. In practice LSA is consumed as morning glory or Hawaiian baby woodrose seeds, which is riskier than the pure-substance figures suggest: alkaloid content varies enormously between seeds and batches, the seeds contain other ergot alkaloids, and commercial seeds are frequently treated with fungicides or insecticides that add their own toxicity. Effects are strongly sedating and often accompanied by intense nausea, vomiting, vasoconstriction and dysphoria. Limited data must never be read as evidence of safety.[3][2]

    Legal Status
    Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status, prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
    Interactions & Contraindications

    Drug interactions

    Ergot alkaloids and vasoconstrictors, Triptans Additive vasoconstriction, a real risk given LSA's alpha-adrenergic and ergoline activity.[3]
    SSRIs, SNRIs, Tramadol, MAOIs Additive serotonergic load, with a theoretical risk of serotonin toxicity.
    Alcohol, Benzodiazepines Additive drowsiness, given LSA's marked sedating character.

    Contraindications

    Cardiovascular disease, hypertension or arrhythmia includes peripheral vascular disease (vasoconstriction risk).[3]
    Pregnancy or breastfeeding ergot alkaloids are uterotonic and abortifacient.
    Personal or family history of psychosis, schizophrenia or bipolar disorder
    Concurrent MAOI, SSRI/SNRI or other serotonergic medication or concurrent vasoconstrictive drugs.
    Usage & Context
    • Traditional entheogenic use of ololiuqui (Turbina/Rivea corymbosa) and related morning glory seeds by Mesoamerican peoples. Contemporary recreational use of morning glory and Hawaiian baby woodrose seeds.
    • Studied as a naturally occurring LSD-like ergoline in receptor-profiling and ethnopharmacology research.
    Sources & Evidence

    Further Information