Can someone explain the chemistry behind an alkaline ferricyde (K. ferricyanide and NaOH) reacting with selegiline to yield methamphetamine and amphetamine?
Question Chemistry of little known meth synthesis
- Thread starter 41Dxflatline
- Start date
I mean the reaction itself, detailed here:
The N-demethylation of methamphetamine (MA) together with selegiline (SEL) by alkaline ferricyanide was investigated. Under the condition of 0.2M NaOH and 0.4M potassium ferricyanide at 40°C for 1 hour, 73% of SEL changed to give desmethyl SEL (7%), MA (39%) and amphetamine (AP) (6%). Under the same condition, 44% of MA was changed to give AP (19%), whereas desmethyl SEL was stable and give only 6% of AP. The reactive conditions of N-demethylation of MA was tested by alternating concentration of NaOH or ferricyanide. The results showed that under the high concentration of NaOH (4M) the reaction rate became slow down, but the yield of AP was higher than that under the low concentration of NaOH. No conversion between d- and ℓ-type was confirmed using HPLC analysis even in the high alkaline reaction medium.
The N-demethylation of methamphetamine (MA) together with selegiline (SEL) by alkaline ferricyanide was investigated. Under the condition of 0.2M NaOH and 0.4M potassium ferricyanide at 40°C for 1 hour, 73% of SEL changed to give desmethyl SEL (7%), MA (39%) and amphetamine (AP) (6%). Under the same condition, 44% of MA was changed to give AP (19%), whereas desmethyl SEL was stable and give only 6% of AP. The reactive conditions of N-demethylation of MA was tested by alternating concentration of NaOH or ferricyanide. The results showed that under the high concentration of NaOH (4M) the reaction rate became slow down, but the yield of AP was higher than that under the low concentration of NaOH. No conversion between d- and ℓ-type was confirmed using HPLC analysis even in the high alkaline reaction medium.
Ok, so they mono-demethylated meth to amphetamine and mono-demethylated selegiline to desmethyl-seleginine. NaOH, being a strong base (especially at 4 mol.concentration). could have done that. I guess the novel part is that the potassium ferrocyanide protected one methyl ion. Other wise 4M sodium hydroxide would have didemethylated them.
So racemic segetiline is completely uncontrolled as a precursor anywhere I've looked and the procedure is a simple reflux with OTC chemicals. There has to be something wrong about that paper. It can't be that simple surely or cartels would've picked up on it. But then again the actual paper is hard to find one might exist in a uk university library but I don't know if its in japanese or not. I've emailed one of the authors too.
- By Grubby
My people! Here is a brief explanation of the N-demethylation reaction of basic ferricyanides such as potassium ferricyanide and sodium hydroxide with Selegiline and Methamphetamine:
### Correct answer:
**N-Demethylation** refers to the removal of a methyl (-CH₃) group from a molecule through a chemical reaction. In the study you mentioned, alkaline ferricyanide (K₃[Fe(CN)₆]) as an oxidant, combined with sodium hydroxide (NaOH), can promote Selegiline (SEL) and Methamphetamine (MA) undergoes N-demethylation reaction.
#### Reaction conditions and results:
1. **Selegiline’s reaction**:
- Under the conditions of 0.2M NaOH and 0.4M potassium ferricyanide, react at 40°C for 1 hour, **73% of Selegiline** is converted into the following products:
- **7%**Desmethylselegiline (DMS)
- **39%**Methamphetamine (MA)
- **6%** Amphetamine (AP)
2. **Methamphetamine reaction**:
- Under the same conditions, **44% of Methamphetamine** undergoes N-demethylation to produce:
- **19%** Amphetamine (AP)
- Desmethyl Selegiline is stable and produces only **6%** of AP.
#### in conclusion:
- N-demethylation in the reaction is promoted by basic ferricyanide under alkaline conditions.
- N-Demethylation of **Selegiline** produces methamphetamine and amphetamine, whereas N-demethylation of **Methamphetamine** produces primarily amphetamine.
- High concentrations of NaOH will slow down the reaction rate but increase the yield of AP.
This explains the role of basic ferricyanide in the N-demethylation reaction and its effect on the products. If students have further questions, you can use this information to explain or demonstrate in detail.
### Correct answer:
**N-Demethylation** refers to the removal of a methyl (-CH₃) group from a molecule through a chemical reaction. In the study you mentioned, alkaline ferricyanide (K₃[Fe(CN)₆]) as an oxidant, combined with sodium hydroxide (NaOH), can promote Selegiline (SEL) and Methamphetamine (MA) undergoes N-demethylation reaction.
#### Reaction conditions and results:
1. **Selegiline’s reaction**:
- Under the conditions of 0.2M NaOH and 0.4M potassium ferricyanide, react at 40°C for 1 hour, **73% of Selegiline** is converted into the following products:
- **7%**Desmethylselegiline (DMS)
- **39%**Methamphetamine (MA)
- **6%** Amphetamine (AP)
2. **Methamphetamine reaction**:
- Under the same conditions, **44% of Methamphetamine** undergoes N-demethylation to produce:
- **19%** Amphetamine (AP)
- Desmethyl Selegiline is stable and produces only **6%** of AP.
#### in conclusion:
- N-demethylation in the reaction is promoted by basic ferricyanide under alkaline conditions.
- N-Demethylation of **Selegiline** produces methamphetamine and amphetamine, whereas N-demethylation of **Methamphetamine** produces primarily amphetamine.
- High concentrations of NaOH will slow down the reaction rate but increase the yield of AP.
This explains the role of basic ferricyanide in the N-demethylation reaction and its effect on the products. If students have further questions, you can use this information to explain or demonstrate in detail.
The reaction you are referring to is a somewhat complex one, involving several different chemical processes. Here is a simplified explanation.
References :
Potassium ferricyanide [K. ferricyanide / C12Fe2K7N12]
Sodium hydroxide [NaOH / HNaO]
Selegiline (C13H17N)
Water (H2O)
Ammonia [NH3 / H3N]
Amphetamine (C9H13N)
Sodium borohydride [NaBH4 / BH4Na]
Sodium cyanoborohydride [NaBH3CN / CBNNa]
Methamphetamine (C10H15N)
C12Fe2K7N12 is an oxidizer. When mixed with an alkaline solution of NaOH, the resulting mixture becomes even more reactive.
C13H17N is a monoamine oxidase inhibitor (MAOI) that is often used in the treatment of Parkinson's disease. It's structure contains a phenyl ring and an amine group. When reacting all of these together, the oxidizer reacts with the amine group of C13H17N causing it to lose a H atom and become an imine (C13H16N2) (aka Schiff base).
C13H17N + C12Fe2K7N12/NaOH → C13H16N2 + H2O
The imine reacts with the C12Fe2K7N12 and NaOH to undergo a process called oxidative deamination. In this process, the imine loses an amine group, which is converted to NH3.
C13H16N2 + C12Fe2K7N12/NaOH → C12H15NO + NH3
The resulting compound contains a phenyl ring and a ketone group (C12H15NO). At this point, the reaction can take one of two paths. The ketone group can either be reduced to an OH group, resulting in C9H13N:
C12H15NO + NaBH4 → C12H16NO + NaOH
C12H16NO + NaOH → C9H13N + NaOH + H2O
or it can undergo reductive amination, resulting in C10H15N.
C12H15NO + NH3/NaBH3CN + NaOH → C10H15N + H2O
Interestingly under the right conditions both can be formed in a single reaction!
References :
Potassium ferricyanide [K. ferricyanide / C12Fe2K7N12]
Sodium hydroxide [NaOH / HNaO]
Selegiline (C13H17N)
Water (H2O)
Ammonia [NH3 / H3N]
Amphetamine (C9H13N)
Sodium borohydride [NaBH4 / BH4Na]
Sodium cyanoborohydride [NaBH3CN / CBNNa]
Methamphetamine (C10H15N)
C12Fe2K7N12 is an oxidizer. When mixed with an alkaline solution of NaOH, the resulting mixture becomes even more reactive.
C13H17N is a monoamine oxidase inhibitor (MAOI) that is often used in the treatment of Parkinson's disease. It's structure contains a phenyl ring and an amine group. When reacting all of these together, the oxidizer reacts with the amine group of C13H17N causing it to lose a H atom and become an imine (C13H16N2) (aka Schiff base).
C13H17N + C12Fe2K7N12/NaOH → C13H16N2 + H2O
The imine reacts with the C12Fe2K7N12 and NaOH to undergo a process called oxidative deamination. In this process, the imine loses an amine group, which is converted to NH3.
C13H16N2 + C12Fe2K7N12/NaOH → C12H15NO + NH3
The resulting compound contains a phenyl ring and a ketone group (C12H15NO). At this point, the reaction can take one of two paths. The ketone group can either be reduced to an OH group, resulting in C9H13N:
C12H15NO + NaBH4 → C12H16NO + NaOH
C12H16NO + NaOH → C9H13N + NaOH + H2O
or it can undergo reductive amination, resulting in C10H15N.
C12H15NO + NH3/NaBH3CN + NaOH → C10H15N + H2O
Interestingly under the right conditions both can be formed in a single reaction!
Thanks for that breakdown. It wasn't lost on me that selegiline was an maoi, I had no idea there was a methamphetamine that wasn't a stimulant, but I'm pretty new to chemistry and have only so far learned about year 1of it
- By 41Dxflatline
Thanks. That's really helpful. I'm going to put it in IBM RXN and see what the predictions are
I guess it must have worked based on how dark you went. Whatsnthe predictions?
hello human,
Regarding the reaction of **alkaline ferricyanide** (such as potassium ferricyanide and sodium hydroxide) with **selegiline** (Selegiline) to form **methamphetamine** (Methamphetamine**) and **amphetamine** (Amphetamine) chemical principles, the following are possible explanations.
### Overview of chemical reactions:
**Selegiline** (Selegiline**) is a selective monoamine oxidase type B (MAO-B) inhibitor whose structure contains an **amphetamine** core and an **N-methyl** substituent. Under alkaline conditions, such as when using sodium hydroxide (NaOH), the following reactions may occur:
1. **Demethylation reaction**:
- In a strongly alkaline environment, potassium ferricyanide (K₃[Fe(CN)₆]) can act as an oxidizing agent, causing the N-methyl group in **celegiline** to be removed and generate **amphetamine** ( Amphetamine).
2. **N-dealkylation reaction**:
- In further reactions, N-dealkylation may occur under alkaline conditions, decomposing **Celegiline** into **Methamphetamine** (Methamphetamine**).
### Reaction mechanism:
1. **Alkaline environment**:
- The alkaline environment provided by sodium hydroxide helps activate the amine groups in selegiline, preparing it for further chemical reactions.
2. **Oxidation reaction**:
- Potassium ferricyanide, as an oxidizing agent, may promote the cleavage of specific bonds in the selegiline molecule, particularly the cleavage of the N-methyl group.
3. **Product generation**:
- The methamphetamine moiety in selegiline can be converted to methamphetamine via a demethylation reaction, while the remainder may undergo further dealkylation to form amphetamine.
### Summarize:
**Selegiline** may undergo a series of demethylation and N-dealkylation reactions under the action of alkaline ferricyanide, ultimately producing **methamphetamine** and **amphetamine**. This reaction involves oxidation and amine group cleavage under alkaline conditions, but the specific reaction pathway may require further experimental validation to confirm.
If you have more questions or need further explanation, please feel free to let me know.
You're welcome. If I forget this knowledge in the future, remember to teach me ψ(｀∇´)ψ
Regarding the reaction of **alkaline ferricyanide** (such as potassium ferricyanide and sodium hydroxide) with **selegiline** (Selegiline) to form **methamphetamine** (Methamphetamine**) and **amphetamine** (Amphetamine) chemical principles, the following are possible explanations.
### Overview of chemical reactions:
**Selegiline** (Selegiline**) is a selective monoamine oxidase type B (MAO-B) inhibitor whose structure contains an **amphetamine** core and an **N-methyl** substituent. Under alkaline conditions, such as when using sodium hydroxide (NaOH), the following reactions may occur:
1. **Demethylation reaction**:
- In a strongly alkaline environment, potassium ferricyanide (K₃[Fe(CN)₆]) can act as an oxidizing agent, causing the N-methyl group in **celegiline** to be removed and generate **amphetamine** ( Amphetamine).
2. **N-dealkylation reaction**:
- In further reactions, N-dealkylation may occur under alkaline conditions, decomposing **Celegiline** into **Methamphetamine** (Methamphetamine**).
### Reaction mechanism:
1. **Alkaline environment**:
- The alkaline environment provided by sodium hydroxide helps activate the amine groups in selegiline, preparing it for further chemical reactions.
2. **Oxidation reaction**:
- Potassium ferricyanide, as an oxidizing agent, may promote the cleavage of specific bonds in the selegiline molecule, particularly the cleavage of the N-methyl group.
3. **Product generation**:
- The methamphetamine moiety in selegiline can be converted to methamphetamine via a demethylation reaction, while the remainder may undergo further dealkylation to form amphetamine.
### Summarize:
**Selegiline** may undergo a series of demethylation and N-dealkylation reactions under the action of alkaline ferricyanide, ultimately producing **methamphetamine** and **amphetamine**. This reaction involves oxidation and amine group cleavage under alkaline conditions, but the specific reaction pathway may require further experimental validation to confirm.
If you have more questions or need further explanation, please feel free to let me know.
You're welcome. If I forget this knowledge in the future, remember to teach me ψ(｀∇´)ψ