Compound: hydrastinine
SMILES: O1c2c(cc3CCN(C(c3c2)O)C)OC1
InChIKey: YOJQZPVUNUQTDF-UHFFFAOYSA-N
Synonyms: hydrastinine, 6592-85-4, 6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol, V1I0L48X6E, NSC-755892, DTXSID3048073, 1,3-Dioxolo(4,5-g)isoquinolin-5-ol, 5,6,7,8-tetrahyro-6-methyl-, 6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-ol, RefChem:414949, DTXCID4028044, 229-533-9, Hydraztinine, 5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-ol, 5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-ol, 1,3-Dioxolo[4,5-g]isoquinolin-5-ol, 5,6,7,8-tetrahydro-6-methyl-, 1,3-DIOXOLO(4,5-g)ISOQUINOLIN-5-OL, 5,6,7,8-TETRAHYDRO-6-METHYL-, EINECS 229-533-9, BRN 0014208, UNII-V1I0L48X6E, Hydrastinin, Spectrum_000377, 6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol, Prestwick0_000195, Prestwick1_000195, Prestwick2_000195, Spectrum2_000742, Spectrum3_001149, Spectrum4_001762, Spectrum5_000343, HYDRASTININE [MI], NCIOpen2_005877, Oprea1_843481, BSPBio_002677, KBioGR_002243, KBioSS_000857, 4-27-00-06396 (Beilstein Handbook Reference), DivK1c_000897, HYDRASTININE [WHO-DD], SCHEMBL308521, SPBio_000724, SPBio_002070, orb1690372, CHEMBL1623232, HY-B1181A, KBio1_000897, KBio2_000857, KBio2_003425, KBio2_005993, KBio3_002177, YOJQZPVUNUQTDF-UHFFFAOYSA-, CHEBI:233287, NINDS_000897, BDBM729096, 1-hydroxy-6,7-methylenedioxy-2-methyl-1,2,3,4-tetrahydroisoquinoline, MFCD00179051, MSK181209, AKOS040758263, US12257253, Compound Hydrastinine, NSC 755892, IDI1_000897, NCGC00178535-02, DA-64312, MS-23130, SBI-0051895.P003, SBI-0051895.P004, CS-0108783, NS00005375, 1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL, F82493, AB00053699_03, AB00053699_04, Q905844, BRD-A57900429-003-05-8, BRD-A57900429-003-06-6, 6-Methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-ol, 6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol #, InChI=1/C11H13NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5,11,13H,2-3,6H2,1H3
Theoretical properties:
molecular_formula: C11H13NO3
molecular_weight: 207.23 g/mol
exact_mass: 207.08954328 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 15
topological_polar_surface_area: 41.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Hydrastinine is an organic molecular entity.
chembl: HYDRASTININE is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
wikipedia: Hydrastinine is a semisynthetic tetrahydroisoquinoline alkaloid made via the nitric acid induced hydrolysis of the alkaloid hydrastine hydrochloride, which is extracted from Hydrastis canadensis L. (Ranunculaceae).  The drug was patented by Bayer as a haemostatic drug during the 1910s.
The first known synthesis of methylenedioxymethamphetamine (MDMA) was actually an intermediate in the synthesis of the methylated analogue of hydrastinine, methylhydrastinine. It was only reviewed for its activity many years after its original synthesis.
Hydrastinine has also been found as a major unwanted side product in MDMA made by the reductive amination of 3,4-methylenedioxyphenylpropan-2-one and methylamine.