1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine, free base - ≥98% , CAS No.28289-54-5

CAS: 28289-54-5 Cat. No.: M338296 Peso molecular: 173.26 Número EC: 248-939-7

GRADE & PURITY ≥98%

Synonyms

AMY23633 | AKOS003657026 | N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine | 1-methyl-4-phenyl-3,6-dihydro-2H-pyridine | BRN 0133712 | J-017031 | CHEBI:17963 | PYRIDINE, 1,2,3,6-TETRAHYDRO-1-METHYL-4-PHENYL- | 1-Methyl-4-phenyl-1,2,5,6-tetrahydropyridine | E

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

A dopaminergic neurotoxin which reportedly causes a severe and irreversible Parkinsonian condition in humans and monkeys.

Specifications

Sinónimos

AMY23633 | AKOS003657026 | N-Methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine | 1-methyl-4-phenyl-3, 6-dihydro-2H-pyridine | BRN 0133712 | J-017031 | CHEBI:17963 | PYRIDINE, 1, 2, 3, 6-TETRAHYDRO-1-METHYL-4-PHENYL- | 1-Methyl-4-phenyl-1, 2, 5, 6-tetrahydropyridine | E

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥98%

Nombres e identificadores

• Sonrisas canónicas: CN1CCC(=CC1)C2=CC=CC=C2
• IUPAC Name: 1-methyl-4-phenyl-3,6-dihydro-2H-pyridine
• InChIKey: PLRACCBDVIHHLZ-UHFFFAOYSA-N
• INCHI: 1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3
• Isómeros SMILES: CN1CCC(=CC1)C2=CC=CC=C2
• Peso molecular: 173.26
• Reaxy-Rn: 133712
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=133712&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Pyridines and derivatives
      • Subclass Hydropyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Pyridines and derivatives
• Subclass: Hydropyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydropyridines
• Alternative Parents: Benzene and substituted derivatives Trialkylamines Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzenoid - Hydropyridine - Monocyclic benzene moiety - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as hydropyridines. These are compounds containing a hydrogenated pyridine ring (i.e. containing less than the maximum number of double bonds.).
• External Descriptors: methylpyridines - tetrahydropyridine - phenylpyridine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

MAOA Tclin Monoamine oxidase A (11911 Activities)

Discover Target: MAOA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MAOB Tclin Monoamine oxidase B (8835 Activities)

Discover Target: MAOB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC6A3 Tclin Dopamine transporter (10535 Activities)

Discover Target: SLC6A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NOS1 Tchem Nitric-oxide synthase, brain (1786 Activities)

Discover Target: NOS1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Objetivos asociados (no humanos)

Nos2 Nitric oxide synthase, inducible (3573 Activities)

Discover Target: Nos2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Qdpr Dihydropteridine reductase (31 Activities)

Discover Target: Qdpr

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc22a5 Solute carrier family 22 member 5 (44 Activities)

Discover Target: Slc22a5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc22a3 Solute carrier family 22 member 3 (35 Activities)

Discover Target: Slc22a3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Drd5 Dopamine receptor (1304 Activities)

Discover Target: Drd5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Maob Monoamine oxidase (439 Activities)

Discover Target: Maob

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in Chloroform, Dichloromethane and Ethyl Acetate
• Punto de ebullición (°C): 128-132° C (lit.) at 12 mmHg
• Punto de fusión (°C): 37-40° C
• Peso molecular: 173.250 g/mol
• XLogP3: 2.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 173.12 Da
• Monoisotopic Mass: 173.12 Da
• Topological Polar Surface Area: 3.200 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 189.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Qiang-Ming Li, Tong Xu, Xue-Qiang Zha, Xiao-Wen Feng, Feng-Yun Zhang, Jian-Ping Luo.  (2023)  Buddlejasaponin IVb ameliorates ferroptosis of dopaminergic neuron by suppressing IRP2-mediated iron overload in Parkinson's disease.  JOURNAL OF ETHNOPHARMACOLOGY,      [PMID:37717841] [10.1016/j.jep.2023.117196]

2. Zhang Mao, Haochen Hui, Xuerong Zhao, Lina Xu, Yan Qi, Lianhong Yin, Liping Qu, Lan Han, Jinyong Peng.  (2023)  Protective effects of dioscin against Parkinson's disease via regulating bile acid metabolism through remodeling gut microbiome/GLP-1 signaling.  Journal of Pharmaceutical Analysis,      [PMID:38024855] [10.1016/j.jpha.2023.06.007]

3. Qiang-Ming Li, Xiang Li, Shuang-Qiao Su, Yu-Tong Wang, Tong Xu, Xue-Qiang Zha, Li-Hua Pan, Zhen-Zi Shang, Feng-Yun Zhang, Jian-Ping Luo.  (2022)  Dendrobine inhibits dopaminergic neuron apoptosis via MANF-mediated ER stress suppression in MPTP/MPP+-induced Parkinson's disease models.  PHYTOMEDICINE,      [PMID:35636177] [10.1016/j.phymed.2022.154193]

4. Wang Wang, Guoxue Zhu, Yuwen Wang, Wei Li, Shilin Yi, Kai Wang, Lu Fan, Juanjuan Tang, Ruini Chen.  (2022)  Multi-Omics Integration in Mice With Parkinson’s Disease and the Intervention Effect of Cyanidin-3-O-Glucoside.  Frontiers in Aging Neuroscience,      [PMID:35572129] [10.3389/fnagi.2022.877078]

5. Tingting Wu, Xianying Fang, Jiahui Xu, Yan Jiang, Fuliang Cao, Linguo Zhao.  (2020)  Synergistic Effects of Ginkgolide B and Protocatechuic Acid on the Treatment of Parkinson’s Disease.  MOLECULES,  25  (17): (3976).  [PMID:32878312] [10.3390/molecules25173976]

6. Shulei Qi, Lina Guo, Jinxin Liang, Kaixuan Wang, Qinghong Liao, Siyu He, Weiping Lyu, Zimeng Cheng, Jiayi Wang, Xiaojia Luo, Xiaomei Yan, Ziyao Lu, Xiaohan Wang, Ziming Wang, Xuehong Chen, Qi Li.  (2024)  A new strategy for the treatment of Parkinson’s disease: Discovery and bio-evaluation of the first central-targeting tyrosinase inhibitor.  BIOORGANIC CHEMISTRY,      [PMID:38986418] [10.1016/j.bioorg.2024.107612]

7. Jie Zhang, Jiahui Shi, Qiubo Yang, Haogang Guo, Lingfeng Guo, Guoliang Zhou, Yinyi Liu, Xiaolei Wang, Xian Hao, Yifei Yang.  (2025)  Nano-magnetoelectric biomimetic system promotes neural differentiation and reverses dopaminergic neuron damage for Parkinson's disease therapy.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.168308]

8. Guoxue Zhu, Wang Wang, Yuwen Wang, Wei Li, Shilin Yi, Kai Wang, Lu Fan, Xinyu Lu, Juanjuan Tang, Ruini Chen.  (2025)  Multi-omics association analysis reveals the pathogenesis of Parkinson's disease and the treatment mechanisms of a medicinal and food plant: Cistanches Herba.  Journal of Future Foods,      [PMID:] [10.1016/j.jfutfo.2024.08.014]

9. Yu Sun, Li Cui, Wanqiu Peng, Rong Chen, Xueneng Guan, Jiangyun Liu.  (2025)  Butyrate-Modified Hyaluronic Acid Ameliorates MPTP-Induced Parkinson’s Disease via Modulating PINK1/Parkin-Involved Mitophagy and Intestinal Flora.  BIOMACROMOLECULES,      [PMID:41324423] [10.1021/acs.biomac.5c00967]

10. Chunlian Liu, Siwen Wang, Haifan Yu, Kai Duo, Chunyu Wang, Jing Jiang, Lin Li.  (2026)  RVG29-Decorated PLGA/Piperine Nanoparticles for Treating Parkinson’s Disease via Restoring Neuronal Energy Metabolism.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.5c05528]