LYSERGIDE

ID: ALA263881

Max Phase: Phase

Molecular Formula: C20H25N3O

Molecular Weight: 323.44

Molecule Type: Small molecule

Associated Items:

Representations

Synonyms (7): D-lsd | Dextrolysergic acid diethylamide | Lsd-25 | Lysergic acid diethylamide | Lysergide | N,n-diethyllysergamide | LSD
Synonyms from Alternative Forms(7):

    Canonical SMILES:  CCN(CC)C(=O)[C@@H]1C=C2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1

    Standard InChI:  InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1

    Standard InChI Key:  VAYOSLLFUXYJDT-RDTXWAMCSA-N

    Associated Targets(Human)

    Serotonin 5a (5-HT5a) receptor 1433 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 1a (5-HT1a) receptor 14969 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2b (5-HT2b) receptor 10323 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 1e (5-HT1e) receptor 696 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 1d (5-HT1d) receptor 2897 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 6 (5-HT6) receptor 9749 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 7 (5-HT7) receptor 5576 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D2 receptor 23596 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D3 receptor 14368 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D4 receptor 7907 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D5 receptor 1597 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Histamine H1 receptor 7573 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Beta-1 adrenergic receptor 6630 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Beta-2 adrenergic receptor 11824 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 1b (5-HT1b) receptor 2801 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2a (5-HT2a) receptor 14758 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2c (5-HT2c) receptor 11471 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Glutaminase kidney isoform, mitochondrial 16997 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Whole blood 398 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Tyrosyl-DNA phosphodiesterase 1 345557 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Associated Targets(non-human)

    Serotonin 7 (5-HT7) receptor 811 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Rattus norvegicus 775804 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin (5-HT) receptor 353 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2 (5-HT2) receptor 2078 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2a (5-HT2a) receptor 3540 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 2c (5-HT2c) receptor 1134 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin receptor 2a and 2b (5HT2A and 5HT2B) 71 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Serotonin 1a (5-HT1a) receptor 8655 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Dopamine D1 receptor 58 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Oryctolagus cuniculus 11301 Activities

    Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

    Molecule Features

    Natural Product: YesOral: NoChemical Probe: NoParenteral: No
    Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
    Chirality: YesAvailability: NoProdrug: No

    Drug Indications

    MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

    Mechanisms of Action

    Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

    Properties

    Molecular Weight: 323.44Molecular Weight (Monoisotopic): 323.1998AlogP: 2.91#Rotatable Bonds: 3
    Polar Surface Area: 39.34Molecular Species: NEUTRALHBA: 2HBD: 1
    #RO5 Violations: 0HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski): 0
    CX Acidic pKa: CX Basic pKa: 7.98CX LogP: 2.28CX LogD: 1.60
    Aromatic Rings: 2Heavy Atoms: 24QED Weighted: 0.94Np Likeness Score: 0.63

    References

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    21. Vermeulen ES, Schmidt AW, Sprouse JS, Wikström HV, Grol CJ..  (2003)  Characterization of the 5-HT(7) receptor. Determination of the pharmacophore for 5-HT(7) receptor agonism and CoMFA-based modeling of the agonist binding site.,  46  (25): [PMID:14640545] [10.1021/jm030826m]
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    23. Glennon RA, Raghupathi R, Bartyzel P, Teitler M, Leonhardt S..  (1992)  Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.,  35  (4): [PMID:1542100] [10.1021/jm00082a014]
    24. Oberlender RA, Kothari PJ, Nichols DE, Zabik JE..  (1984)  Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane.,  27  (6): [PMID:6737421] [10.1021/jm00372a015]
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