The Vespiary

The Hive => Chemistry Discourse => Topic started by: raybeez on February 14, 2003, 02:14:00 AM

Title: Reducing to GHB
Post by: raybeez on February 14, 2003, 02:14:00 AM

Hello,

SWIM has obtained some quantity of NaBH4 and was wondering if there was a good compound that could be reduced with it to form GHB. SWIM noticed that in

Post 364288 (https://www.thevespiary.org/talk/index.php?topic=6911.msg36428800#msg36428800)

(Rhodium: "GABA -> GBL + GHB", Chemistry Discourse), Rhodium mentions succinic acid monomethyl ester giving a 90% yield with NaBH4 in H2O. Would this be a relatively straight forward reaction to do? Just add excess reducing agent slowly, then purify out final product?

SWIM was wondering if something like 4-Oxo butyric acid would work (SWIM thinks that's how it's named.. just GHB with an aldehyde group instead of an alcohol).

Not sure how easy it would be to find these compounds, but the yield seems good..

Title: succinic semialdehyde
Post by: Rhodium on February 14, 2003, 02:34:00 AM

The aldehyde you refer to is called "succinic semialdehyde".

Title: succinic semialdehyde
Post by: raybeez on February 14, 2003, 02:47:00 AM

Interesting. Swim did a search on google, and found that succinic semialdehyde is a part of GABA metabolism. Swim found that a genetic disorder causing a deficiency of the enzyme Succinic semialdehyde dehydrogenase (SSADH) "leads to abnormal accumulation of the compound succinic semialdehyde, which is reduced or converted to 4-hydroxybutyric acid" (

http://www.peacehealth.org/kbase/nord/nord1113.htm (http://www.peacehealth.org/kbase/nord/nord1113.htm)

)

Could you simply just consume this compound and have it elevate GHB levels in your body? People missing the enzyme suffer seizures and other neurological problems, but that might be due to an excessive, long term build up of the GHB. Either way, sounds like it could be reduced by NaBH4..

Title: Re: Swim found that a genetic disorder causing
Post by: M3Psych on February 18, 2003, 06:14:00 PM

---

Swim found that a genetic disorder causing a deficiency of the enzyme Succinic semialdehyde dehydrogenase (SSADH) "leads to abnormal accumulation of the compound succinic semialdehyde, which is reduced or converted to 4-hydroxybutyric acid"

---

The condition is called GHB aciduria and it's not known whether or not the symptoms are due to increased plasma levels of GHB or of increased plasma levels of GHB are the result.

---

Could you simply just consume this compound and have it elevate GHB levels in your body?

---

It's probably possible with enough NADH in the body.

---

People missing the enzyme suffer seizures and other neurological problems, but that might be due to an excessive, long term build up of the GHB.

---

Again, it's not known if the excess GHB is a cause of the condition or simply an effect of it.