174418-82-7 Usage
Description
7-Hydroxy Mitragynine is a terpenoid indole alkaloid derived from the plant Mitragyna speciosa, commonly known as Kratom. It is a minor constituent of this plant and exhibits a higher potency than mitragynine in various tests. The compound possesses opioid agonistic activity with a potency 30and 17-fold higher than that of mitragynine and morphine, respectively, making it a significant alkaloid in the context of its pharmacological properties.
Uses
Used in Pharmaceutical Applications:
7-Hydroxy Mitragynine is used as an active alkaloid for its potent opioid agonistic activity. Its high affinity for A-opioid receptors in binding assays and its higher potency compared to mitragynine and morphine make it a valuable compound for the development of pharmaceutical products targeting opioid receptors.
Used in Pain Management:
Due to its potent opioid agonistic activity, 7-Hydroxy Mitragynine is used as an analgesic agent for pain management. Its higher potency compared to other opioids suggests potential applications in the treatment of severe pain conditions, where conventional opioids may not be as effective.
Used in Research and Development:
7-Hydroxy Mitragynine serves as an important compound in the research and development of new drugs targeting the opioid system. Its unique properties and high potency make it a valuable tool for understanding the mechanisms of opioid action and for the development of novel therapeutic agents with improved efficacy and reduced side effects.
Used in Drug Delivery Systems:
Similar to gallotannin, 7-Hydroxy Mitragynine could potentially benefit from novel drug delivery systems to enhance its applications and efficacy. The development of carriers such as organic and metallic nanoparticles could improve the delivery, bioavailability, and therapeutic outcomes of 7-Hydroxy Mitragynine in various applications, including pain management and pharmaceutical research.
Preparation
7-Hydroxymitragynine is produced by oxidation of mitragynine and is a minor constituent (< 0.01% in fresh leaves) found at concentrations of up to 2% in leaf extracts and commercial kratom products; however, it is believed to be the major contributor to the known addictive potential of kratom given its activity as a potent μ-opioid receptor agonist.
Pharmacokinetics
Mitragynine and 7-hydroxymitragynine are partial agonists at the mu-opioid receptor. Human studies demonstrate the analgesic effects of kratom, while kratom extract, mitragynine and 7-hydroxymitragynine have been shown to be antinociceptive in animal models. The antinociceptive effects are reversed by an opioid antagonist.Mitragynine also binds to adrenergic receptors, serotonergic and dopamine receptors. Although there is limited information regarding its effects at these receptors, kratom extracts and mitragynine have been reported in animal studies to have a variety of non-opioid-like behavioural effects, including antidepressant and antipsychotic effects.
Check Digit Verification of cas no
The CAS Registry Mumber 174418-82-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,4,4,1 and 8 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 174418-82:
(8*1)+(7*7)+(6*4)+(5*4)+(4*1)+(3*8)+(2*8)+(1*2)=147
147 % 10 = 7
So 174418-82-7 is a valid CAS Registry Number.
174418-82-7Relevant articles and documents
A new indole alkaoid, 7alpha-hydroxy-7H-mitragynine, from Mitragyna speciosa in Thailand
Ponglux,Wongseripipatana,Takayama,Kikuchi,Kurihara,Kitajima,Aimi,Sakai Shin ichiro
, p. 580 - 581 (1994)
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Stereochemical assignment of pseudoindoxyl alkaloids
Takayama, Hiromitsu,Kurihara, Mika,Subhadhirasakul, Sanan,Kitajima, Mariko,Aimi, Norio,Sakai, Shin-Ichiro
, p. 87 - 92 (1996)
The stereochemistries of the C2 and C3 positions in three pseudoindoxyl alkaloids, i.e., mitragynine pseudoindoxyl, yohimbine pseudoindoxyl, and β-yohimbine pseudoindoxyl, were elucidated by spectroscopic analyses. The CD spectra of these compounds and that of fluorocarpamine showed the antipodal-like curves in the long wavelength region.
Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: Discovery of opioid agonists structurally different from other opioid ligands
Takayama, Hiromitsu,Ishikawa, Hayato,Kurihara, Mika,Kitajima, Mariko,Aimi, Norio,Ponglux, Dhavadee,Koyama, Fumi,Matsumoto, Kenjiro,Moriyama, Tomoyuki,Yamamoto, Leonard T.,Watanabe, Kazuo,Murayama, Toshihiko,Horie, Syunji
, p. 1949 - 1956 (2002)
Mitragynine (1) is a major alkaloidal component in the Thai traditional medicinal herb, Mitragyna speciosa, and has been proven to exhibit analgesic activity mediated by opioid receptors. By utilizing this natural product as a lead compound, synthesis of some derivatives, evaluations of the structure-activity relationship, and surveys of the intrinsic activities and potencies on opioid receptors were performed with guinea pig ileum. The affinities of some compounds for μ-, δ-, and κ-receptors were determined in a receptor binding assay. The essential structural moieties in the Corynanthe type indole alkaloids for inducing the opioid agonistic activity were also clarified. The oxidative derivatives of mitragynine, i.e., mitragynine pseudoindoxyl (2) and 7-hydroxymitragynine (12), were found as opioid agonists with higher potency than morphine in the experiment with guinea pig ileum. In addition, 2 induced an analgesic activity in the tail flick test in mice.
DEUTERATED MITRAGYNINE ANALOGS AS SAFER OPIOID MODULATORS IN THE MITRAGYNINE CLASS
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Page/Page column 73-75, (2020/08/22)
The present invention provides a compound having the structure: or a pharmaceutically acceptable salt or ester thereof, and methods of using the compound to treat pain, depressive disorders, mood disorders, anxiety disorders, opioid use disorder, and opioid withdrawal symptoms.
