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SM-102

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SM-102
Names
Preferred IUPAC name
Heptadecan-9-yl 8-{(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino}octanoate
Identifiers
3D model (JSmol)
UNII
  • InChI=1S/C44H87NO5/c1-4-7-10-13-16-17-18-24-32-41-49-43(47)35-29-25-31-38-45(39-40-46)37-30-23-19-22-28-36-44(48)50-42(33-26-20-14-11-8-5-2)34-27-21-15-12-9-6-3/h42,46H,4-41H2,1-3H3
    Key: BGNVBNJYBVCBJH-UHFFFAOYSA-N
  • CCCCCCCCCCCOC(=O)CCCCCN(CCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCC)CCO
Properties
C44H87NO5
Molar mass 710.182 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

SM-102 (heptadecan-9-yl 8-((2-hydroxyethyl) (6-oxo-6-(undecyloxy) hexyl) amino) octanoate) is an ionizable amino lipid that has been used in combination with other lipids in the formation of lipid nanoparticles. Administration of luciferase with mRNA in SM-102-containing lipid nanoparticles induces hepatic luciferase expression in mice. Formulations containing SM-102 have been used in the development of lipid nanoparticles for delivery of mRNA-based vaccines.[1][2][3]

SM-102 is part of the Moderna COVID-19 vaccine.[4] However, the research chemical, luciferase, is not part of the Moderna covid vaccine.[5], and as such require the material safety data sheet to reflect the hazards of the solvent. [6] On May 19th, 2021 Cayman Chemical Company, a producer of the lipid, released a statement noting that there are multiple grades of SM-102 available. Their statement went on to affirm that the lipid, for use in cases where it is an active pharmaceutical ingredient, follows Good Manufacturing Practice. [7] As well, according to Dr. Nicholas Davidson, who is a physician and lipid biologist at Washington University in St. Louis; chloroform is used as a transport solvent and would not be a part of any vaccine makeup. [8]

SM-102 in Chloroform
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H302, H315, H319, H331, H351, H361, H372
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
0
0

References

  1. ^ Safety and Immunogenicity Study of 2019-nCoV Vaccine (mRNA-1273) for Prophylaxis of SARS-CoV-2 Infection (COVID-19), clinicaltrials.gov (US NIH/NLM), identifier NCT04283461. Accessed Jan. 17, 2021.
  2. ^ Clinical study protocol mRNA-1273-P301, Amendment 6, ModernaTX, Inc., Dec. 23, 2020; accessed on line Jan. 17, 2021.
  3. ^ COVID-19 Vaccines: Update on Allergic Reactions, Contraindications, and Precautions, Clinician Outreach and Communication Activity (COCA) Webinar, Wednesday, December 30, 2020, CDC (US HHS); accessed on line Jan. 17, 2021.
  4. ^ FACT SHEET FOR RECIPIENTS AND CAREGIVERS
  5. ^ {{cite web |url= https://www.reuters.com/article/factcheck-moderna-luciferin-idUSL1N2MT265 |title= Fact Check-Moderna’s COVID-19 vaccine does not contain luciferin
  6. ^ SM-102 Material Safety Data Sheet, Cayman Chemical Company, Apr. 11 2021; accessed on line May 25, 2021.
  7. ^ SM-102 for Research Use Only (RUO), Cayman Chemical Company, May 19, 2021; accessed on line May 25, 2021.
  8. ^ Moderna vaccine ingredient falsely targeted as unsafe, AP NEWS, May 19, 2021; accessed on line May 25, 2021.
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