# SMILES-Prompting: A Novel Approach to LLM Jailbreak Attacks in Chemical Synthesis

arXiv: https://arxiv.org/abs/2410.15641 · HTML: https://mlsanity.com/paper/2410.15641/

## Key facts

- Cited by 7 papers in the map (data through 14 Oct 2026).
- Placed in Jailbreaking, one of 12 directions in LLM safety and security.
- Builds on 25 of its 30 references that are in the map.
- First posted on arXiv 21 Oct 2024.

## Placed in

- LLM safety and security / [Jailbreaking](https://mlsanity.com/safety/jailbreaking/)

## Builds on (most cited first, 25 of 25)

- [Evaluating Large Language Models Trained on Code](https://mlsanity.com/paper/2107.03374/) (2021)
- [Do As I Can, Not As I Say: Grounding Language in Robotic Affordances](https://mlsanity.com/paper/2204.01691/) (2022)
- [The Rise and Potential of Large Language Model Based Agents: A Survey](https://mlsanity.com/paper/2309.07864/) (2023)
- [Jailbreaking Black Box Large Language Models in Twenty Queries](https://mlsanity.com/paper/2310.08419/) (2023)
- [RealToxicityPrompts: Evaluating Neural Toxic Degeneration in Language Models](https://mlsanity.com/paper/2009.11462/) (2020)
- [Red Teaming Language Models with Language Models](https://mlsanity.com/paper/2202.03286/) (2022)
- [Ignore Previous Prompt: Attack Techniques For Language Models](https://mlsanity.com/paper/2211.09527/) (2022)
- [Out of One, Many: Using Language Models to Simulate Human Samples](https://mlsanity.com/paper/2209.06899/) (2022)
- [Red Teaming Language Models to Reduce Harms: Methods, Scaling Behaviors, and Lessons Learned](https://mlsanity.com/paper/2209.07858/) (2022)
- [ChemCrow: Augmenting large-language models with chemistry tools](https://mlsanity.com/paper/2304.05376/) (2023)
- ["Do Anything Now": Characterizing and Evaluating In-The-Wild Jailbreak Prompts on Large Language Models](https://mlsanity.com/paper/2308.03825/) (2023)
- [Jailbreak and Guard Aligned Language Models with Only Few In-Context Demonstrations](https://mlsanity.com/paper/2310.06387/) (2023)
- [GPT-4 Is Too Smart To Be Safe: Stealthy Chat with LLMs via Cipher](https://mlsanity.com/paper/2308.06463/) (2023)
- [DeepInception: Hypnotize Large Language Model to Be Jailbreaker](https://mlsanity.com/paper/2311.03191/) (2023)
- [Exploiting Programmatic Behavior of LLMs: Dual-Use Through Standard Security Attacks](https://mlsanity.com/paper/2302.05733/) (2023)
- [Red-Teaming Large Language Models using Chain of Utterances for Safety-Alignment](https://mlsanity.com/paper/2308.09662/) (2023)
- [Defending Large Language Models Against Jailbreaking Attacks Through Goal Prioritization](https://mlsanity.com/paper/2311.09096/) (2023)
- [Attacks, Defenses and Evaluations for LLM Conversation Safety: A Survey](https://mlsanity.com/paper/2402.09283/) (2024)
- [ChemLLM: A Chemical Large Language Model](https://mlsanity.com/paper/2402.06852/) (2024)
- [FLIRT: Feedback Loop In-context Red Teaming](https://mlsanity.com/paper/2308.04265/) (2023)
- [Use of LLMs for Illicit Purposes: Threats, Prevention Measures, and Vulnerabilities](https://mlsanity.com/paper/2308.12833/) (2023)
- [Spinning Language Models: Risks of Propaganda-As-A-Service and Countermeasures](https://mlsanity.com/paper/2112.05224/) (2021)
- [Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition](https://mlsanity.com/paper/2311.16119/) (2023)
- [Latent Jailbreak: A Benchmark for Evaluating Text Safety and Output Robustness of Large Language Models](https://mlsanity.com/paper/2307.08487/) (2023)
- [BadLlama: cheaply removing safety fine-tuning from Llama 2-Chat 13B](https://mlsanity.com/paper/2311.00117/) (2023)

## Built on by (most cited first, 7 of 7)

- [Alignment and Safety in Large Language Models: Safety Mechanisms, Training Paradigms, and Emerging Challenges](https://mlsanity.com/paper/2507.19672/) (2025)
- [AntiDote: Bi-level Adversarial Training for Tamper-Resistant LLMs](https://mlsanity.com/paper/2509.08000/) (2025)
- [SciRisk-Bench: A Risk-Dimension-Aware Benchmark for AI4Science Safety](https://mlsanity.com/paper/2606.18936/) (2026)
- [The Dual-use Dilemma in LLMs: Do Empowering Ethical Capacities Make a Degraded Utility?](https://mlsanity.com/paper/2501.13952/) (2025)
- [Malicious Repurposing of Open Science Artefacts by Using Large Language Models](https://mlsanity.com/paper/2601.18998/) (2026)
- [onepot-Bench 0: towards lab-aware in silico chemistry benchmarks](https://mlsanity.com/paper/2608.02595/) (2026)
- [SafeMol: Dual-Modality Safety Alignment for Molecular Multimodal Models](https://mlsanity.com/paper/2609.33640/) (2026)

## Abstract (arXiv)

The increasing integration of large language models (LLMs) across various fields has heightened concerns about their potential to propagate dangerous information. This paper specifically explores the security vulnerabilities of LLMs within the field of chemistry, particularly their capacity to provide instructions for synthesizing hazardous substances. We evaluate the effectiveness of several prompt injection attack methods, including red-teaming, explicit prompting, and implicit prompting. Additionally, we introduce a novel attack technique named SMILES-prompting, which uses the Simplified Molecular-Input Line-Entry System (SMILES) to reference chemical substances. Our findings reveal that SMILES-prompting can effectively bypass current safety mechanisms. These findings highlight the urgent need for enhanced domain-specific safeguards in LLMs to prevent misuse and improve their potential for positive social impact.