Huperzine A

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  • Identifiers

    CAS number
    102518-79-6

    Molecular formula
    C15H18N2O

    SMILES
    C/C=C/1\[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 41.38%
    Roasted 27.09%
    Burnt 21.79%
    Animal 21.7%
    Nutty 21.1%
    Spicy 19.3%
    Earthy 18.88%
    Bitter 18.65%
    Musty 18.37%
    Meaty 18.16%

     

    Flavor
    Bitter 73.64%
    Cedarleaf 20.7%
    Nitrile 20.42%
    Very strong 20.27%
    Indole 20.05%
    Basil 19.92%
    Lovage 19.83%
    Alkaline 19.23%
    Cereal 19.15%
    Shrimp 19.14%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    8.36 (weak base)

    Molecular weight
    242.32 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    427°C

    Melting point expt.

    • 217-219 °C

    Flash point

    • 242.92 ˚C est.

  • Synonyms

    • Huperzine A
    • (-)-huperzine A
    • 102518-79-6
    • (-)-huperazine A
    • L-huperzine A
    • Huperzine-A
    • Hup A
    • Kimpukan A
    • DTXSID8046038
    • DTXCID6026038
    • CHEBI:78330
    • 0111871I23
    • 5,9-Methanocycloocta[b]pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R,9R,11E)-
    • (1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
    • (5R,9R,11E)-5-AMINO-11-ETHYLIDENE-5,6,9,10-TETRAHYDRO-7-METHYL-5,9-METHANOCYCLOOCTA(B)PYRIDIN-2(1H)-ONE
    • 5,9-Methanocycloocta(b)pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R,9R,11E)-
    • (1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo(7.3.1.02,7)trideca-2(7),3,10-trien-5-one
    • RefChem:788584
    • 600-320-6
    • Selagine
    • Huperzin A
    • CHEMBL395280
    • Huperizine A
    • (5R,9R,E)-5-Amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one
    • (5R,9R,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one
    • 1369-64-8
    • CAS-102518-79-6
    • 120786-18-7
    • Cerebra
    • Hyperazzine A
    • MFCD01714949
    • 1vot
    • NCGC00159362-02
    • HUP
    • HUPERAINE A
    • HUPERZINE A [MI]
    • HUPERZINE A [VANDF]
    • HUPERZINE A [WHO-DD]
    • SCHEMBL136368
    • SPECTRUM1505255
    • CHEBI:94624
    • GTPL13727
    • Tox21_111603
    • BDBM50199522
    • CCG-40292
    • EBC-26288
    • UNII-0111871I23
    • AKOS016842839
    • Tox21_111603_1
    • (+-)-HA
    • DB04864
    • EBC-611075
    • SDCCGMLS-0066755.P001
    • NCGC00263655-01
    • AS-15723
    • H1700
    • NS00023157
    • A11941
    • EN300-33171546
    • Q425198
    • BRD-K62240499-001-02-6
    • BRD-K97618845-001-03-1
    • (-)-1-Amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one(Huperzine A)
    • (-)1-Amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one( (-)-Huperzine A)
    • (1R,9R)-1-Amino-13-eth-(E)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one
    • (1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0,2,7]trideca-2(7),3,10-trien-5-one
    • (1R,9R,13E)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0,2,7]trideca-2(7),3,10-trien-5-one
    • (huperazine A)(-)-1-Amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one
    • (R)-1-Amino-13-eth-(E)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one
    • (R)-1-Amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one
    • 1-Amino-13-eth-(E)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one
    • 1-Amino-13-eth-(Z)-ylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one
    • 1-Amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one
    • 1-Amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one((+/-)-Huperzine A)
    • 1-Amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0*2,7*]trideca-2(7),3,10-trien-5-one((-)-Huperzine A)
    • 1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0~2,7~]trideca-2(7),3,10-trien-5-one
    • 5,9-Methanocycloocta(b)pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R-(5-alpha,9-beta,11E))-
    • 102518-79-6

  • Applications

    Huperzine A (CAS 102518-79-6) is a natural alkaloid of interest primarily in pharmaceutical R&D and nutraceuticals due to its reversible acetylcholinesterase inhibiting activity, which informs exploration of cognitive-support applications and brain-function studies. In practice, it is used as a research and development ingredient in drug discovery programs and as a dietary supplement component in markets where permitted, while also serving as a reference material for quality control and analytical characterization of botanical extracts. In chemical research, Huperzine A may function as a benchmark for alkaloid synthesis and as a reagent in enzymology and pharmacology assays related to acetylcholinesterase inhibition. Its use is typically constrained by local regulations and formulation limits, and it is not claimed as a healthcare remedy.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.48
    methanol 16.79
    isopropanol 4.27
    water 0.15
    ethyl acetate 10.6
    n-propanol 7.46
    acetone 9.59
    n-butanol 6.66
    acetonitrile 7.26
    DMF 52.54
    toluene 3.82
    isobutanol 5.83
    1,4-dioxane 24.45
    methyl acetate 10.72
    THF 52.67
    2-butanone 11.8
    n-pentanol 5.42
    sec-butanol 3.08
    n-hexane 0.06
    ethylene glycol 5.84
    NMP 66.43
    cyclohexane 0.11
    DMSO 44.35
    n-butyl acetate 13.02
    n-octanol 2.86
    chloroform 16.46
    n-propyl acetate 8.74
    acetic acid 25.31
    dichloromethane 17.26
    cyclohexanone 31.96
    propylene glycol 6.45
    isopropyl acetate 7.61
    DMAc 43.51
    2-ethoxyethanol 19.91
    isopentanol 7.09
    n-heptane 0.12
    ethyl formate 15.18
    1,2-dichloroethane 9.92
    n-hexanol 8.56
    2-methoxyethanol 48.63
    isobutyl acetate 8.52
    tetrachloromethane 2.18
    n-pentyl acetate 12.1
    transcutol 56.87
    n-heptanol 6.4
    ethylbenzene 1.41
    MIBK 8.89
    2-propoxyethanol 44.61
    tert-butanol 4.92
    MTBE 1.73
    2-butoxyethanol 25.37
    propionic acid 14.29
    o-xylene 2.27
    formic acid 22.09
    diethyl ether 2.17
    m-xylene 3.66
    p-xylene 2.36
    chlorobenzene 8.06
    dimethyl carbonate 12.96
    n-octane 0.07
    formamide 28.1
    cyclopentanone 51.25
    2-pentanone 10.53
    anisole 5.69
    cyclopentyl methyl ether 11.07
    gamma-butyrolactone 71.18
    1-methoxy-2-propanol 30.8
    pyridine 24.65
    3-pentanone 7.03
    furfural 68.66
    n-dodecane 0.1
    diethylene glycol 47.61
    diisopropyl ether 0.79
    tert-amyl alcohol 3.19
    acetylacetone 20.65
    n-hexadecane 0.12
    acetophenone 11.61
    methyl propionate 14.02
    isopentyl acetate 14.81
    trichloroethylene 30.78
    n-nonanol 3.42
    cyclohexanol 5.92
    benzyl alcohol 12.67
    2-ethylhexanol 5.15
    isooctanol 5.55
    dipropyl ether 2.62
    1,2-dichlorobenzene 8.2
    ethyl lactate 11.12
    propylene carbonate 31.61
    n-methylformamide 33.03
    2-pentanol 2.59
    n-pentane 0.07
    1-propoxy-2-propanol 23.26
    1-methoxy-2-propyl acetate 25.34
    2-(2-methoxypropoxy) propanol 20.44
    mesitylene 1.85
    ε-caprolactone 32.11
    p-cymene 2.71
    epichlorohydrin 59.65
    1,1,1-trichloroethane 7.59
    2-aminoethanol 11.9
    morpholine-4-carbaldehyde 70.21
    sulfolane 67.58
    2,2,4-trimethylpentane 0.09
    2-methyltetrahydrofuran 17.33
    n-hexyl acetate 11.3
    isooctane 0.1
    2-(2-butoxyethoxy)ethanol 27.37
    sec-butyl acetate 5.8
    tert-butyl acetate 8.45
    decalin 0.16
    glycerin 20.16
    diglyme 44.39
    acrylic acid 18.5
    isopropyl myristate 3.91
    n-butyric acid 22.12
    acetyl acetate 10.31
    di(2-ethylhexyl) phthalate 10.66
    ethyl propionate 7.47
    nitromethane 48.27
    1,2-diethoxyethane 10.91
    benzonitrile 15.77
    trioctyl phosphate 6.68
    1-bromopropane 2.81
    gamma-valerolactone 91.87
    n-decanol 2.56
    triethyl phosphate 7.74
    4-methyl-2-pentanol 2.98
    propionitrile 8.16
    vinylene carbonate 36.55
    1,1,2-trichlorotrifluoroethane 50.29
    DMS 15.4
    cumene 1.5
    2-octanol 3.04
    2-hexanone 7.95
    octyl acetate 6.16
    limonene 2.89
    1,2-dimethoxyethane 23.45
    ethyl orthosilicate 6.86
    tributyl phosphate 6.83
    diacetone alcohol 17.78
    N,N-dimethylaniline 4.85
    acrylonitrile 16.36
    aniline 10.98
    1,3-propanediol 19.61
    bromobenzene 6.5
    dibromomethane 7.15
    1,1,2,2-tetrachloroethane 19.84
    2-methyl-cyclohexyl acetate 11.75
    tetrabutyl urea 9.5
    diisobutyl methanol 2.89
    2-phenylethanol 17.28
    styrene 1.5
    dioctyl adipate 8.24
    dimethyl sulfate 25.09
    ethyl butyrate 8.92
    methyl lactate 17.67
    butyl lactate 15.66
    diethyl carbonate 7.73
    propanediol butyl ether 18.19
    triethyl orthoformate 8.3
    p-tert-butyltoluene 2.38
    methyl 4-tert-butylbenzoate 16.84
    morpholine 30.32
    tert-butylamine 1.59
    n-dodecanol 1.83
    dimethoxymethane 33.31
    ethylene carbonate 25.89
    cyrene 32.01
    2-ethoxyethyl acetate 23.35
    2-ethylhexyl acetate 10.81
    1,2,4-trichlorobenzene 12.81
    4-methylpyridine 21.61
    dibutyl ether 2.03
    2,6-dimethyl-4-heptanol 2.89
    DEF 13.61
    dimethyl isosorbide 39.56
    tetrachloroethylene 12.81
    eugenol 22.37
    triacetin 17.2
    span 80 16.46
    1,4-butanediol 7.37
    1,1-dichloroethane 6.23
    2-methyl-1-pentanol 6.01
    methyl formate 29.13
    2-methyl-1-butanol 5.56
    n-decane 0.14
    butyronitrile 7.83
    3,7-dimethyl-1-octanol 3.54
    1-chlorooctane 1.09
    1-chlorotetradecane 0.51
    n-nonane 0.1
    undecane 0.12
    tert-butylcyclohexane 0.17
    cyclooctane 0.06
    cyclopentanol 9.4
    tetrahydropyran 10.23
    tert-amyl methyl ether 1.81
    2,5,8-trioxanonane 31.85
    1-hexene 0.38
    2-isopropoxyethanol 13.04
    2,2,2-trifluoroethanol 14.56
    methyl butyrate 10.83

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction