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Chemical compound
Pharmaceutical compound
Hydrastinine |
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Pregnancy
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| ATC code | |
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| Metabolism | Hepatic |
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| Excretion | Renal |
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6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol
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| CompTox Dashboard (EPA) | |
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| ECHA InfoCard | 100.026.849  |
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| Formula | C11H13NO3 |
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| Molar mass | 207.229 g·mol−1 |
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| 3D model (JSmol) | |
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O1c2c(OC1)cc3c(c2)CCN(C3O)C
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InChI=1S/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  YKey:YOJQZPVUNUQTDF-UHFFFAOYSA-N Y
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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.[1]
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.[2]
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| Phenethylamines | |
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| Amphetamines | |
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| Phentermines | |
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| Cathinones | |
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Phenylisobutylamines
(and further-extended) | |
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Catecholamines
(and close relatives) | |
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Cyclized
phenethylamines | | Phenylalkylpyrrolidines | |
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2-Benzylpiperidines
(phenidates) | |
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Phenylmorpholines
(phenmetrazines) | |
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Phenyloxazolamines
(aminorexes) | |
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Isoquinolines and
tetrahydroisoquinolines | |
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| 2-Aminoindanes | |
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| 2-Aminotetralins | |
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| Others / unsorted |
- 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, bromojimscaline, jimscaline)
- 2-ADN
- 2-Benzhydrylpyrrolidine
- 2C-B-5-hemiFLY-α6 (BNAP)
- 2C-B-PYR
- 2CBecca
- 2CJP
- 2CLisaB
- 2CLisaH
- 3-Benzazepines (e.g., fenoldopam, lorcaserin, 7-chlorolorcaserin, SCHEMBL5334361)
- 3-Benzhydrylmorpholine
- 3-Phenylpiperidines (e.g., 3-phenylpiperidine, 3-PPP, OSU-6162 (PNU-96391), LPH-5, LPH-48, Z3517967757 (Z7757))
- 6-AB
- AL-1095
- Aminochromes (e.g., adrenochrome, adrenolutin)
- Benzocyclobutenes (e.g., 2CBCB-NBOMe, bromotomscaline, S33005, TCB-2, tomscaline)
- Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
- Butyltolylquinuclidine
- Camfetamine
- Cypenamine (trans-2-phenylcyclopentylamine)
- Diphenidine
- Diphenylprolinol
- DMBMPP
- Ergolines (e.g., LSD)
- Fencamfamin
- GYKI-52895
- HDMP-29
- Ivabradine
- Methoxphenidine
- Methylmorphenate
- Milnacipran
- MT-45
- 2-Naphthylamine
- Org 6582
- Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, DEMPDHPCA-2C-D, RU-27251)
- PF-592,379
- Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine)
- Phenylpiracetams (e.g., phenylpiracetam, MRZ-9547, RGPU-95)
- Pyridopyrroloquinoxalines (e.g., lumateperone, deulumateperone, IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549)
- Tetrahydrobenzopyranylamines (e.g., CT-5126)
- Tolazoline
- Tricyclics (e.g., AMDA, AMDH, benzoctamine, dizocilpine, SpAMDA)
- ZC-B
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| Related compounds |
- 2-Furylethylamine
- 2-Pyrrolylethylamine
- 3-Pyrrolylethylamine
- 3-Pyrrolylpropylamine
- 2-Tetrahydrofurylethylamine
- 4-Benzylpiperidine
- 7-AB
- Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane)
- Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline)
- Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide)
- Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine)
- Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine)
- Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine, CT-4719, ORG-37684)
- Phenylalkenylamines (e.g., phenylbutenamine)
- Phenylalkynylamines (e.g., phenylbutynamine)
- Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine)
- Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA)
- Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone)
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