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Mitragynine Picrate is an alkaloid derived from the Mitragyna speciosa Korth plant, which is known for its stimulant and opiate-like effects depending on the dosage. This amorphous compound forms a series of crystalline salts and derivatives, with the picrate form appearing as thin, orange-red needles. Mitragynine Picrate exerts a general depressant effect on plain muscle and facilitates the passage of autonomic impulses, but is ineffective against pathogenic organisms. It is a white to off-white solid.

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  • 4098-40-2 Structure
  • Basic information

    1. Product Name: MITRAGYNINE PICRATE
    2. Synonyms: 9-Methoxycorynantheidine;MITRAGYNINE(SH);Mitragynin;MITRAGYNINE(P);(αE,2S,3S,12bS)-3-Ethyl-1,2,3,4,6,7,12,12b-octahydro-8-Methoxy-α-(MethoxyMethylene)-indolo[2,3-a]quinolizine-2-acetic Acid Methyl Ester;16,17-Didehydro-9,17-diMethoxy-corynan-16-carboxylic Acid Methyl Ester;(16E,20beta)-16,17-Didehydro-9,17-dimethoxy-corynan-16-carboxylic acid methyl ester;MITRAGYNINE(AS)
    3. CAS NO:4098-40-2
    4. Molecular Formula: C23H30N2O4
    5. Molecular Weight: 627.6
    6. EINECS: 200-659-6
    7. Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Neurochemicals;Alkaloids
    8. Mol File: 4098-40-2.mol
  • Chemical Properties

    1. Melting Point: 92-95°C
    2. Boiling Point: bp5 230-240°
    3. Flash Point: 9℃
    4. Appearance: /
    5. Density: 1.22±0.1 g/cm3 (20 ºC 760 Torr)
    6. Vapor Pressure: 1.39E-12mmHg at 25°C
    7. Refractive Index: 1.604
    8. Storage Temp.: -20°C Freezer
    9. Solubility: Chloroform (Slightly), Methanol (Slightly)
    10. PKA: 18.35±0.60(Predicted)
    11. CAS DataBase Reference: MITRAGYNINE PICRATE(CAS DataBase Reference)
    12. NIST Chemistry Reference: MITRAGYNINE PICRATE(4098-40-2)
    13. EPA Substance Registry System: MITRAGYNINE PICRATE(4098-40-2)
  • Safety Data

    1. Hazard Codes: F,T
    2. Statements: 11-23/24/25-39/23/24/25-36/37/38-22
    3. Safety Statements: 7-16-36/37-45-26
    4. RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
    5. WGK Germany: 1
    6. RTECS:
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 4098-40-2(Hazardous Substances Data)

4098-40-2 Usage

Uses

1. Used in Pharmaceutical Industry:
Mitragynine Picrate is used as a neurochemical for its stimulant and opiate-like effects, depending on the dosage. It is currently being investigated for its potential in treating hard drug addiction.
2. Used in Research and Development:
Mitragynine Picrate is used as a research compound to study its effects on the central nervous system and its potential applications in the treatment of various conditions related to the nervous system.
3. Used in Drug Formulation:
Mitragynine Picrate, in its various salt forms, can be used in the formulation of drugs targeting the central nervous system, particularly those aimed at treating addiction and related disorders.
4. Used in Toxicological Studies:
Due to its depressant effect on plain muscle and its interaction with autonomic impulses, Mitragynine Picrate can be used in toxicological studies to understand its potential side effects and safety profile.
5. Used in Quality Control and Standardization:
The various crystalline forms of Mitragynine Picrate, such as the hydrochloride and methiodide, can be used for quality control and standardization purposes in the pharmaceutical industry to ensure the consistency and purity of the compound in drug formulations.

References

Field., J. Chern. Soc., 119,887 (1921)Raymond-Hamet, Millat., Bull. sci. pharrnacol., 40, 593 (1933)lng, Raison., J. Chern. Soc., 986 (1939)Loudon., Chern. Soc. Spec. Publ., 3, 12 (1955)Hendrickson., Chern. & Ind., 713 (1961)Joshi, Raymond-Hamet, Taylor., ibid, 573 (1963)Pharmacology: Grewal., J. Pharrn. expo Ther., 46,251 (1932)

Check Digit Verification of cas no

The CAS Registry Mumber 4098-40-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,0,9 and 8 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 4098-40:
(6*4)+(5*0)+(4*9)+(3*8)+(2*4)+(1*0)=92
92 % 10 = 2
So 4098-40-2 is a valid CAS Registry Number.
InChI:InChI=1/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14-,16+,19+/m1/s1

4098-40-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Mitragynine

1.2 Other means of identification

Product number -
Other names MITRAGYNINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4098-40-2 SDS

4098-40-2Relevant articles and documents

MITRAGYNINE ANALOGS FOR THE TREATMENT OF PAIN, MOOD DISORDERS AND SUBSTANCE USE DISORDERS

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Page/Page column 54; 60; 70, (2020/03/05)

The present invention provides a compound having the structure (I): or a pharmaceutically acceptable salt or ester thereof, and a method of treating a subject afflicted with pain a depressive disorder, a mood disorder or an anxiety disorder by administering the compound to the subject.

MITRAGYNINE ALKALOIDS AS OPIOID RECEPTOR MODULATORS

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Page/Page column 74; 78; 79, (2017/10/13)

The present invention provides a compound having the structure: or a pharmaceutically acceptable salt or ester thereof, and a method of treating a subject afflicted with pain, a depressive disorder, a mood disorder or an anxiety disorder by administering the compound to the subject.

Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators

Kruegel, Andrew C.,Gassaway, Madalee M.,Kapoor, Abhijeet,Váradi, András,Majumdar, Susruta,Filizola, Marta,Javitch, Jonathan A.,Sames, Dalibor

, p. 6754 - 6764 (2016/06/14)

Mu-opioid receptor agonists represent mainstays of pain management. However, the therapeutic use of these agents is associated with serious side effects, including potentially lethal respiratory depression. Accordingly, there is a longstanding interest in the development of new opioid analgesics with improved therapeutic profiles. The alkaloids of the Southeast Asian plant Mitragyna speciosa, represented by the prototypical member mitragynine, are an unusual class of opioid receptor modulators with distinct pharmacological properties. Here we describe the first receptor-level functional characterization of mitragynine and related natural alkaloids at the human mu-, kappa-, and delta-opioid receptors. These results show that mitragynine and the oxidized analogue 7-hydroxymitragynine, are partial agonists of the human mu-opioid receptor and competitive antagonists at the kappa- and delta-opioid receptors. We also show that mitragynine and 7-hydroxymitragynine are G-protein-biased agonists of the mu-opioid receptor, which do not recruit β-arrestin following receptor activation. Therefore, the Mitragyna alkaloid scaffold represents a novel framework for the development of functionally biased opioid modulators, which may exhibit improved therapeutic profiles. Also presented is an enantioselective total synthesis of both (-)-mitragynine and its unnatural enantiomer, (+)-mitragynine, employing a proline-catalyzed Mannich-Michael reaction sequence as the key transformation. Pharmacological evaluation of (+)-mitragynine revealed its much weaker opioid activity. Likewise, the intermediates and chemical transformations developed in the total synthesis allowed the elucidation of previously unexplored structure-activity relationships (SAR) within the Mitragyna scaffold. Molecular docking studies, in combination with the observed chemical SAR, suggest that Mitragyna alkaloids adopt a binding pose at the mu-opioid receptor that is distinct from that of classical opioids.

Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction

Kerschgens, Isabel P.,Claveau, Elise,Wanner, Martin J.,Ingemann, Steen,Van Maarseveen, Jan H.,Hiemstra, Henk

supporting information, p. 12243 - 12245 (2013/01/16)

The pharmacologically interesting indole alkaloids (-)-mitragynine, (+)-paynantheine and (+)-speciogynine were synthesised in nine steps from 4-methoxytryptamine by a route featuring (i) an enantioselective thiourea-catalysed Pictet-Spengler reaction, providing the tetrahydro-β- carboline ring and (ii) a Pd-catalysed Tsuji-Trost allylic alkylation, closing the D-ring. The Royal Society of Chemistry 2012..

Indole Alkaloid Derivatives Having Opioid Receptor Agonistic Effect, and Therapeutic Compositions and Methods Relating to Same

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Page/Page column 9; 17, (2009/09/08)

Indole alkaloid derivatives having an opioid receptor agonistic effect, their synthesis, and therapeutic compositions containing these derivatives, and methods of treating conditions with these compounds and therapeutic compositions, are provided.

General approach to the total synthesis of 9-methoxy-substituted indole alkaloids: Synthesis of mitragynine, as well as 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol

Ma, Jun,Yin, Wenyuan,Zhou, Hao,Liao, Xuebin,Cook, James M.

experimental part, p. 264 - 273 (2009/04/10)

(Chemical Equation Presented) Herein, the full details of the synthesis of the 9-methoxy-substituted Corynanthe indole alkaloids mitragynine (1), 9-methoxygeissoschizol (3), and 9-methoxy-Nb-methylgeissoschizol (4) are described. Initially, an efficient synthetic route to the optically active 4-methoxytryptophan ethyl ester 20 on a multigram scale was developed via a Mori-Ban-Hegedus indole synthesis. The ethyl ester of D-4-methoxytryptophan 20 was obtained with a radical-mediated regioselective bromination of indoline 12 serving as a key step. Alternatively, the key 4-methoxytryptophan intermediate 22 could be synthesized by the Larock heteroannulation of aryl iodide 10b with the internal alkyne 21a. The use of the Boc-protected aniline 10b was crucial to the success of this heteroannulation. The α,β-unsaturated ester 6 was synthesized via the Pictet-Spengler reaction as the pivotal step. This was followed by a Ni(COD)2-mediated cyclization to set up the stereocenter at C-15. The benzyloxy group in 31 was removed to provide the intermediate ester 5. This chiral tetracyclic ester 5 was employed to accomplish the first total synthesis of 9-methoxygeissoschizol (3) and 9-methoxy-N b-methylgeissoschizol (4) as well as the opioid agonistic indole alkaloid mitragynine (1).

Total synthesis of the opioid agonistic indole alkaloid mitragynine and the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-N b-methylgeissoschizol

Ma, Jun,Yin, Wenyuan,Zhou, Hao,Cook, James M.

, p. 3491 - 3494 (2008/02/12)

An enantiospecific method for the synthesis of 4-methoxytryptophan has been developed via a regiospecific Larock heteroannulation and employed for the first total syntheses of 9-methoxygeissoschizol and 9-methoxy-N b-methylgeissoschizol, as well as the total synthesis of the opioid agonistic alkaloid mitragynine. The asymmetric Pictet-Spengler reaction and a Ni(COD)2-mediated cyclization served as key steps.

New procedure to mask the 2,3-π bond of the indole nucleus and its application to the preparation of potent opioid receptor agonists with a corynanthe skeleton

Takayama, Hiromitsu,Misawa, Kaori,Okada, Naoki,Ishikawa, Hayato,Kitajima, Mariko,Hatori, Yoshio,Murayama, Toshihiko,Wongseripipatana, Sumphan,Tashima, Kimihito,Matsumoto, Kenjiro,Horie, Syunji

, p. 5705 - 5708 (2007/10/03)

(Diagram presented) Treatment of indole alkaloids with hypervalent iodine in the presence of ethylene glycol provides 2,3-ethylene glycol bridged adducts that could be converted into the original indoles under mild reductive conditions. This procedure, which involves masking of the reactivity of the indole nucleus at the β-position, was utilized for the modification of the benzene ring of the indoline derivative and was applied to the preparation of potent opioid receptor agonists with the Corynanthe skeleton.

The first total synthesis of (-)-mitragynine, an analgesic indole alkaloid in Mitragyna speciosa

Takayama,Maeda,Ohbayashi,Kitajima,Sakai,Aimi

, p. 9337 - 9340 (2007/10/02)

Starting from an optically pure alcohol, (R)-(3), which was prepared by enzymatic hydrolysis of the racemic acetate (2) or enantioselective reduction of the ketone derivative (4), the chiral total synthesis of mitragynine (1), a major corynanthe-type indole alkaloid having an analgesic effect in Mitragyna speciosa, was accomplished.