Rotundine - ≥98% , CAS No.483-14-7

CAS: 483-14-7 Cat. No.: R136626 Formula: C₂₁H₂₅NO₄ Molecular Weight: 355.43 EC Number: 811-160-3 PubChem CID: 72301

GRADE & PURITY ≥98%

Synonyms

(-)-2,3,9,10-Tetramethoxyberbine | 13a-alpha-Berbine, 2,3,9,10-tetramethoxy- | 6H-Dibenzo(a,g)quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (S)- | Gindarine | tetrahydropalmatine | SW219613-1 | (-)-rotundine | Tetrahydropalmatine, dl- | (S)-(

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

(-)-2,3,9,10-Tetramethoxyberbine | 13a-alpha-Berbine, 2,3,9,10-tetramethoxy- | 6H-Dibenzo(a,g)quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (S)- | Gindarine | tetrahydropalmatine | SW219613-1 | (-)-rotundine | Tetrahydropalmatine, dl- | (S)-(

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Potent, selective dopamine D 1 receptor antagonist (K i = 124 nM). Lower affinity for D 2 and D 3 receptors. Potent 5-HT 1A receptor antagonist (K i = 340 nM). Adrenergic, anti-arrhythmic, antihypertensive and antipsychotic agent. Active in vivo and in vi

Storage

Room temperature

Shipped In

Normal

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

Pubchem Sid

488184687

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488184687

Canonical Smiles

COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC

IUPAC Name

(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline

InChIKey

AEQDJSLRWYMAQI-KRWDZBQOSA-N

INCHI

1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

Isomeric SMILES

COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC

PubChem CID

72301

Molecular Weight

355.43

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Protoberberine alkaloids and derivatives

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Protoberberine alkaloids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Protoberberine alkaloids and derivatives
• Alternative Parents: Tetrahydroisoquinolines Anisoles Aralkylamines Alkyl aryl ethers Trialkylamines Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Protoberberine skeleton - Tetrahydroprotoberberine skeleton - Tetrahydroisoquinoline - Anisole - Alkyl aryl ether - Aralkylamine - Benzenoid - Tertiary amine - Tertiary aliphatic amine - Ether - Azacycle - Organoheterocyclic compound - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Hydrocarbon derivative - Amine - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
• External Descriptors: Isoquinoline alkaloids

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

Associated Targets(Human)

F3 Tclin Tissue factor (1 Activities)

Discover Target: F3

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

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

HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

Discover Target: HTR1A

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

DRD2 Tclin Dopamine D2 receptor (23596 Activities)

Discover Target: DRD2

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

DRD1 Tclin Dopamine D1 receptor (9720 Activities)

Discover Target: DRD1

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

DRD4 Tchem Dopamine D4 receptor (7907 Activities)

Discover Target: DRD4

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

HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

Discover Target: HTR2A

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

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

Discover Target: ADRA1A

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

DRD3 Tclin Dopamine D3 receptor (14368 Activities)

Discover Target: DRD3

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

DRD5 Tchem Dopamine D5 receptor (1597 Activities)

Discover Target: DRD5

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

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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

Coagulation factor III (5 Activities)

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

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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

Staphylococcus aureus (210822 Activities)

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Plasmodium falciparum (966862 Activities)

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

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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

Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: -283° (C=1,EtOH)
• Melt Point(°C): 142 °C
• Molecular Weight: 355.400 g/mol
• XLogP3: 3.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 355.178 Da
• Monoisotopic Mass: 355.178 Da
• Topological Polar Surface Area: 40.200 Ų
• Heavy Atom Count: 26
• Formal Charge: 0
• Complexity: 475.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• 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

Frequently Asked Questions

How should this product be stored?

Store at room temperature.

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 483-14-7, the molecular formula is C21H25NO4, and the molecular weight is 355.43 g/mol. InChIKey AEQDJSLRWYMAQI-KRWDZBQOSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.