Isomiosamine

CAS 53844-46-5

MF C9H10N2 MW
146.19 g/mol

3-(3,4-dihydro-2H-pyrrol-2-yl)pyridine

(+/-)-Isomyosmine

rac-(3R)-3-(3,4-dihydro-2H-pyrrol-2-yl)pyridine
tumor necrosis factor alpha (TNFα) inhibitor, MyMD-1, MYMD-1, Isomyosamine, 3A50Y1J4LP, MyMD Pharmaceuticals

synthetic derivative of tobacco alkaloids

Isomyosamine, also known as MyMD-1 or MYMD-1, is a synthetic derivative of tobacco plant alkaloids being developed as a metabolic- and immunomodulator by MyMD Pharmaceuticals. To date, isomyosamine has been shown to suppress the production of IFN-γ, IL-2, IL-10, and TNF-α, and decrease the severity of experimental thyroiditis in a murine model.^[1] Trials in humans are being planned, and some are underway, examining the potential benefits of isomyosamine in autoimmune diseases such as rheumatoid arthritis, and in sarcopenia and frailty.^[2]

MyMD Pharmaceuticals claim that MYMD-1 is not immunosuppressive, and thus should not be associated with the dangerous side effects such as infections that are seen in currently used TNF-α inhibitors such as adalimumab.^[3] While it is true that there currently is no evidence of immunosuppression in isomyosamine recipients, this has not yet been tested in large clinical trials

Safety and Efficacy of Isomyosamine in Reducing Inflammation and Treating Muscle Loss in Older Adults After Hip or Thigh Bone Fractures

CTID: NCT06942182

Phase: Phase 2

Status: Not yet recruiting

Date: 2025-04-24

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2016161051&_cid=P11-ML35LH-80616-1

Isomyosmine

[08] Isomyosmine (3-(3,4-dihydro-2H-pyrrol-2-yl)-pyridine) is a nicotine related alkaloid present in solanecea plants containing nicotine.

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US211193045&_cid=P11-ML35LH-80616-1

Unless otherwise clear from context, all percentages referred to herein are expressed as percent by weight based on the total weight of the composition. Percentages expressed herein as “w/v” refer to mass, in grams, of the component per 100 ml of solvent. For example, a 1% (w/v) composition of isomyosmine contains lg (1000 mg) of isomyosmine per 100 ml of solvent, which is equivalent to 10 mg/ml.

Isomyosmine (3-(3,4-dihydro-2H-pyrrol-2-yl)-pyridine) is a nicotine related alkaloid present in solanecea plants containing nicotine.

Isomyosmine may be prepared synthetically using known techniques, and also is commercially available from several chemical suppliers. Isomyosmine has two optical isomers (+/−) owing to an asymmetric carbon atom within its pyrrole ring that joins to the pyridine ring. Unless otherwise clear from context, the term “isomyosmine,” as used herein, is inclusive of enantiomeric mixtures (+/−) including racemic mixtures, as well as isolated forms of one or the other enantiomer.

In some embodiments, isomyosmine may be adsorbed on a cation exchange resin such as polymethacrilic acid (Amberlite IRP64 or Purolite C115HMR), as described in U.S. Pat. No. 3,901,248, the disclosure of which is hereby incorporated by reference in its entirety. Such cation exchange resins have been used commercially, for example, in nicotine replacement therapy, e.g., nicotine polacrilex.

PAT

• Method of Treating Substance AddictionsPublication Number: US-2017333415-A1Priority Date: 2015-02-19
• Method of treating addictions to opioidsPublication Number: US-10471052-B2Priority Date: 2015-02-19Grant Date: 2019-11-12
• Method of treating cocaine addictionPublication Number: US-11331310-B2Priority Date: 2015-02-19Grant Date: 2022-05-17
• Method of treating disorders associated with chronic inflammationPublication Number: US-2021106578-A1Priority Date: 2015-03-31
• Method of Treating Substance AddictionsPublication Number: US-2020215045-A1Priority Date: 2015-02-19
• Compositions for e-cigarettesPublication Number: WO-2016133890-A1Priority Date: 2015-02-19
• Method of treating substance addictionsPublication Number: US-9884055-B2Priority Date: 2015-02-19Grant Date: 2018-02-06
• Method of Treating Substance AddictionsPublication Number: US-2018140590-A1Priority Date: 2015-02-19
• Methods of treating sarcopeniaPublication Number: US-11219620-B2Priority Date: 2015-03-31Grant Date: 2022-01-11
• Methods of Treating Apoptosis and Altering Programmed Cell DeathPublication Number: US-2018021321-A1Priority Date: 2015-03-31
• Methods of reversing normal aging process and extending lifespanPublication Number: US-11179382-B2Priority Date: 2015-03-31Grant Date: 2021-11-23
• Method of treating viral infectionsPublication Number: US-10786493-B2Priority Date: 2015-03-31Grant Date: 2020-09-29
• Methods of treating cancer, autoimmune disorders, and other conditions associated with chronic inflammationPublication Number: CN-107666907-BPriority Date: 2015-03-31Grant Date: 2022-05-13

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Scientific studies

Preclinical studies

One preliminary murine study comparing isomyosamine to rapamycin, the best-characterised drug slowing the progression of aging, reported an increase in lifespan in the isomyosamine cohort, indicating anti-aging activity. Isomyosamine’s anti-proliferative effects were similar to those of rapamycin.^[4]

Clinical trials

A phase I randomised double-blind placebo-controlled trial on healthy volunteers examining the safety and pharmacokinetic properties of different amounts of isomyosamine found no serious adverse events, but 3 cases of mild dysgeusia in the highest-dose (600 mg) cohort. A preliminary decrease in TNF-α levels was reported in the lowest-dose (150 mg) cohort, but not in the placebo cohort.^[5]

Identifiers
CAS Number	53844-46-5
3D model (JSmol)	Interactive image
ChemSpider	9461533
PubChem CID	11286546
UNII	3A50Y1J4LP
CompTox Dashboard (EPA)	DTXSID80461155
InChI
SMILES
Properties
Chemical formula	C9H10N2
Molar mass	146.193 g·mol−1
Related compounds
Related compounds	Myosmine Nicotine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).Infobox references

References

1.  Di Dalmazi, Giulia; Chalan, Paulina; Caturegli, Patrizio (2019-03-01). “MYMD-1, a Novel Immunometabolic Regulator, Ameliorates Autoimmune Thyroiditis via Suppression of Th1 Responses and TNF-α Release”. The Journal of Immunology. 202 (5): 1350–1362. doi:10.4049/jimmunol.1801238. ISSN 0022-1767. PMID 30674573. S2CID 59226562.
2.  “MyMD Pharmaceuticals® Provides Dosing Update on Phase 2 Multi-Center Clinical Trial of MYMD-1® as a Therapy for Delaying Aging and Extending Healthy Lifespan”. MyMD. Retrieved 2023-08-13.
3.  “MYMD-1®”. MyMD. Retrieved 2023-08-13.
4.  Sabini, Elena; O’Mahony, Alison; Caturegli, Patrizio (2023-02-24). Anderson, Rozalyn M (ed.). “MyMD-1 Improves Health Span and Prolongs Life Span in Old Mice: A Noninferiority Study to Rapamycin”. The Journals of Gerontology: Series A. 78 (2): 227–235. doi:10.1093/gerona/glac142. ISSN 1079-5006. PMID 35914953.
5.  Brager, Jenna; Chapman, Chris; Dunn, Leonard; Kaplin, Adam (2022-11-11). “A Double-blind, Placebo-controlled, Randomized, Single Ascending, and Multiple Dose Phase 1 Study to Evaluate the Safety, Tolerability, and Pharmacokinetics of Oral Dose Isomyosamine Capsules in Healthy Adult Subjects”. Drug Research. 73 (2): 95–104. doi:10.1055/a-1962-6834. ISSN 2194-9379. PMC 9902179. PMID 36368677.

/////////////isomiosamine, tumor necrosis factor alpha (TNFα) inhibitor, MyMD-1, MYMD-1, Isomyosamine, 3A50Y1J4LP, MyMD Pharmaceuticals, ANAX, ADVECT, BLUE JET

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